Novak Djokovic

At the 2020 ATP Cup, Djokovic helped Serbia win its first title by scoring six victories including wins over Medvedev in the semifinal and Nadal in the final. At the 2020 Australian Open, he defeated long time rival Roger Federer in straight sets en route to the final where he defeated three-time grand slam runner-up Dominic Thiem in five sets. This is Djokovic's 8th win at the Australian Open, making him the first Open Era male player to win Grand Slam titles in three different decades. For his 17th Grand Slam win he received 2.5 Million Euro as prize money. Djokovic won the title at Dubai Tennis Championships fifth time, defeating Stefanos Tsitsipas in the final.

Current through the 2020 Dubai Tennis Championships.

After a triumphant grass season, Djokovic started his North American hardcourt swing with a third round showing at the Rogers Cup, losing against eventual runner-up Stefanos Tsitsipas in a 2-hour, 16-minute three-setter. Afterwards, he returned to play the Cincinnati Masters for the first time in three years. In an event plagued by suspended play due to rain, Djokovic defeated defending champion Grigor Dimitrov in the third round and Milos Raonic in the quarterfinals back to back in three sets. Djokovic went on to defeat Marin Cilic in the semifinals in a fourth consecutive three set match, setting up his sixth appearance at the finals of the tournament and fourth final against seven-time champion Roger Federer. Although Federer was riding a streak of 100 consecutive holds of serve at the tournament, Djokovic went on to break his serve three times and win his first Cincinnati Masters title convincingly in straight sets. With this victory, Djokovic became the first (and, as of 2019, only) player in tennis history to complete the career Golden Masters—a feat achieved by winning all nine ATP Masters 1000 events at least once in one's career.

At Wimbledon, he won his sixteenth Grand Slam, defending his title to win the tournament for a fifth time by defeating Roger Federer in an epic five set final that lasted four hours and fifty seven minutes, the longest in Wimbledon history. Djokovic saved two championship points in the fifth set en route to winning the title and the match also marked the first time a fifth set tiebreak was played in the men's singles of Wimbledon at 12 games all. Djokovic then played at the 2019 Cincinnati Open as the defending champion and reached the semifinal where he lost to eventual champion Daniil Medvedev in three sets. At the 2019 US Open, Djokovic was unable to defend his title, falling to Stan Wawrinka in the fourth round, while down two sets and a break before retiring due to injury. The defeat prevented Djokovic from winning three of the four Grand Slam events that year, a feat that he achieved in 2011 and 2015. In October 2019, Djokovic defeated John Millman in straight sets to win the Japan Open. At the Shanghai Masters, Djokovic reached the quarterfinal stage, but lost to Stefanos Tsitsipas in three sets. In November 2019, Djokovic reached final of Paris Masters after defeating Grigor Dimitrov in straight sets. In the final, Djokovic claimed his fifth title in Paris Masters after a two set win over Canadian young star Denis Shapovalov. Djokovic then played in the Björn Borg group at the 2019 ATP Finals but was eliminated in the round robin stage after a straight-sets win over Matteo Berrettini, a three-set loss to Dominic Thiem and a straight sets defeat to Federer (his first loss to Federer since 2015).

At the 2019 Australian Open, Djokovic defeated Nadal in straight sets in the final.

At the 2019 Wimbledon Championships, Djokovic bested Federer in five sets in an almost 5 hour match.

Their most recent Grand Slam tournament meeting was in the second round of the 2019 Australian Open. Djokovic defeated Tsonga in straight sets.

On 30 June 2019, Djokovic confirmed that he added former world No. 2 and Wimbledon champion Goran Ivanišević to his coaching team.

In January he won against Dominic Thiem in straight sets at the Kooyong Classic exhibition tournament. At the 2018 Australian Open, the Serbian won in the second round against Gael Monfils and then in the third round eliminated Albert Ramos Viñolas in straight sets, before bowing out in close straight sets against Chung Hyeon from South Korea. In late January, he underwent surgery on his elbow. On 3 March, he announced on Twitter he was back on the practice courts, and with a little over one week practice, he surprisingly played Indian Wells, losing in the second round to Taro Daniel. He later had another second-round loss in the Miami Open, this time to Benoît Paire.

He competed in the French Open, reaching the semifinals without dropping a set and recording wins over Hubert Hurkacz, Henri Laaksonen, Salvatore Caruso, Jan-Lennard Struff, and fifth seed Alexander Zverev. His fourth round win over Struff made him the first man to reach 10 consecutive quarterfinals at Roland Garros. In the semifinals, he faced 2018 finalist Dominic Thiem, who defeated Djokovic in a four-hour, five-set match that was interrupted by rain multiple times and stretched across two days. This ended his 26-match winning streak in major tournaments and brought his search for a second Nole Slam to an end.

At the 2018 Wimbledon Championships, the two faced each other in the semifinals. This match became their second-longest match and just their third five-set meeting, stretching for 5 hours and 17 minutes over two days. Djokovic broke Nadal in the final game of the fifth set to win 10–8, after saving three break points at 7–7 which would have allowed Nadal to serve for the match. This was Nadal's first defeat in the semifinals of a Grand Slam since the 2009 US Open, and his first ever defeat in the semifinals of Wimbledon.

In January, Djokovic defended his title in Doha defeating new world No. 1 Andy Murray in three sets. At the 2017 Australian Open, he was upset in the second round by No. 117 Denis Istomin of Uzbekistan. This was the first time since 2007 that Djokovic had failed to reach the quarterfinals at the Australian Open, and the first time ever in his career that he had lost to a player ranked outside of the top 100 in a Grand Slam tournament. In February and March, Djokovic played at the Mexican Open and the Indian Well Masters, but in both events was eliminated by Nick Kyrgios, in the third and fourth rounds, respectively. In April, Djokovic reached the quarterfinals of the Monte-Carlo Masters, losing to David Goffin. After the tournament, he decided to split with his long-time coach Marián Vajda, fitness specialist Gebhard Phil-Gritsch and physioterapeut Miljan Amanović, citing the need to find a winning spark. A better showing at the Madrid Masters saw Djokovic reach the semi-finals, losing to Nadal in straight sets. A runner-up result at the Rome Masters indicated solid improvements in his form.

On 21 May 2017, he announced that Andre Agassi would become his new coach, starting at the 2017 French Open. However, as the defending champion, he lost at Roland Garros in the quarterfinals to Dominic Thiem. He prepared for Wimbledon at the Eastbourne International, playing his first non-Wimbledon tournament on grass since the 2010 Aegon Championships. He won the tournament, beating Gaël Monfils in the final. This marked his first grass title outside of Wimbledon. He made it to the quarterfinals at Wimbledon before retiring against Tomas Berdych while down a set and a break, due to an elbow injury which he said had been bothering him for a year and a half.

On 26 July, Djokovic announced that he would miss the 2017 US Open and the rest of the 2017 season to fully recover from his elbow injury.

Seeded second at the Shanghai Masters, he defeated Jérémy Chardy, 16th seed Marco Cecchinato, 7th seed Kevin Anderson, 4th seed Alexander Zverev, and 13th seed Borna Ćorić in a decisive run. He did not drop a set nor have his serve broken during the tournament. This was his fourth title in Shanghai and second Masters title of the year. With this win, he overtook Roger Federer and returned to the #2 ranking for the first time since the 2017 French Open. On 31 October, Rafael Nadal announced his withdrawal from the 2018 Paris Masters due to an abdominal injury. As a result, Djokovic reclaimed the World No. 1 ranking.

On 5 May 2017, Djokovic confirmed that he had come to a mutual agreement to terminate his coaching relationship with Vajda, as well as Phil-Gritsch and Amanović. In a statement on his website, Djokovic cited the reasons for the personnel shakeup: "Novak and the team members decided to part ways after a detailed analysis of the game, achieved results in the previous period, and also after discussing private plans of each team member. Despite the fantastic cooperation so far, Djokovic felt he needed to make a change, and to introduce new energy in order to raise his level of play."

On 22 May 2017, Djokovic was unveiled as a brand ambassador of Lacoste after a five-year partnership with Uniqlo.

Djokovic began his French Open campaign with a straight three sets win over David Goffin in the first round and also defeated Guido Pella in straight sets in the second round. In the third round, Djokovic defeated Dimitrov in three sets. In the fourth round he came back from a set down and defeated Philipp Kohlschreiber of Germany in four sets and in the process he had reached a 16th consecutive Grand Slam quarterfinal. Djokovic then lost to Nadal in the semi-final in five sets.

On 3 April 2016, Djokovic won the 2016 Miami Open for the third consecutive year, and did so without dropping a set en route to his sixth career Miami Open title, tying him with Andre Agassi for most ever Miami Open men's singles titles. In addition, 2016 marked the third consecutive year that Djokovic swept both Indian Wells and the Miami Open, the first male singles player to ever do that. This was also the fourth time in his career Djokovic won both Miami and Indian Wells back-to-back. His finals win in Miami saw Djokovic surpass Roger Federer to become the all-time leading prize money winner on the ATP tour with career earnings of $98.2 million. After an early round exit at the Monte Carlo Masters, Djokovic quickly bounced back by winning the Madrid title for the second time in his career with a three set victory over Murray. They met again in the Rome Masters final one week later with Murray the victor, despite a sluggish performance, Djokovic defeated Nadal and Nishikori in two long quarterfinals and semi-finals.

Djokovic defeated Andy Murray in the final of the 2016 French Open in four sets, making him the reigning champion of all four major tournaments, a historic feat the media dubbed the "Nole Slam." With his French Open triumph, Djokovic became the 8th player in history (and the second oldest) to achieve a Career Grand Slam, the third player in history to hold all four Grand Slam titles at the same time, and the first player to win $100 million in prize money. However, at Wimbledon, his major win streak came to an end in the third-round when he lost to American Sam Querrey in four sets. It was his earliest exit in a Grand Slam since the 2009 French Open.

Djokovic was the #6 seed entering the US Open. This was his first appearance at the US Open since the 2016 final. He defeated Márton Fucsovics, Tennys Sandgren, Richard Gasquet, and João Sousa to reach the quarterfinals, where he was expected to face Roger Federer; however, Federer was upset by John Millman, who Djokovic then defeated in straight sets. Djokovic thus advanced to his eleventh US Open semifinal in as many appearances. He overcame Kei Nishikori in straight sets to reach his eighth US Open final, where he faced #3 seed Juan Martín del Potro. He defeated del Potro in straight sets to win his third US Open title and second Grand Slam title of the year. This win returned him to the top 3 in the world rankings for the first time since the 2017 French Open.

The two would also meet in the 2016 Australian Open semi-finals, where Djokovic played virtually flawless tennis in the first two sets to eventually claim a four set victory en route to capturing a record 6th Australian Open and his 11th Grand Slam title.

In the 2016 clay court season, Djokovic and Murray met in the final of the 2016 Mutua Madrid Open, where Djokovic captured his record-breaking 29th Masters 1000 title in three sets. One week later, however, Murray comfortably beat Djokovic in straight sets in the 2016 Internazionali BNL d'Italia final, denying Djokovic his 30th Masters 1000 crown and interrupting his path to becoming the first player to break through the 100 million dollar prize Money Mark. At the apex of the clay court season, the 2016 French Open, Djokovic and Murray met once again at the final. Despite losing the first set 3–6, Djokovic went on to win the next three sets 6–1, 6–2, 6–4 and claim his maiden French Open title. This win completed Djokovic's Career Grand Slam and denied Murray his first French Open title.

In May 2015, right after winning his fourth Rome Masters title, Djokovic launched a line of nutritional food products, called Djokolife. On 10 April 2016, while in town for the Monte-Carlo Masters, Djokovic opened a vegan restaurant called Eqvita in Monte Carlo. The restaurant reportedly closed in March 2019.

Djokovic collected his 60th career title in Doha, defeating Nadal in two sets in a final that lasted 73 minutes. He broke his own ATP ranking points record, bringing it up to 16,790. Djokovic then proceeded to win his sixth Australian Open. On his road to his Open Era record sixth title in Melbourne, he defeated Roger Federer in four sets in the semi-finals, and in a rematch of the 2015 final, he defeated Andy Murray, in three straight sets. He quickly rebounded from an eye infection at the Dubai open to collect a fifth Indian Wells Masters title, defeating Rafael Nadal in the semi-finals, and Milos Raonic in the final. Djokovic's run was so dominant that Nos. 2 and 3 (Andy Murray and Roger Federer) could have combined their points and still not have had enough to pass him.

At the 2015 French Open, Djokovic finally defeated nine-time champion and five-time consecutive defending champion at the French Open, thus ending Nadal's 39-match win streak at this tournament. He became only the second man in history to have defeated Nadal at the tournament (after Robin Söderling in 2009), and the first to do so in straight sets.

In April 2015, Henman offered another comment on Djokovic's standing among the all-time greats, saying "it's only a matter of time before he is considered alongside Federer and Nadal as one of the greatest players of all time". Having proclaimed him "one of the all-time greats" in November 2014, John McEnroe put Djokovic in all-time top five following his 2015 Wimbledon win, Djokovic's ninth Grand Slam tournament title: "My top four are Laver, Sampras, Roger and Nadal but Novak is at number five and rising". Andrew Castle stated in January 2016 that Djokovic is "undoubtedly moving towards being considered the sport's all-time greatest player". In June 2016, a panel of more than forty ESPN tennis analysts ranked Djokovic as number eight on their top twenty all-time combined list of both male and female tennis players; he was number five among the males, behind Federer, Laver, Sampras, and Borg. Rod Laver said in 2016 that Djokovic was tied with Federer as the best player of all time. In February 2018, Djokovic got placed No. 5 by Tennis.com in their list of 50 greatest male players of the Open era, behind Federer, Laver, Nadal, and Sampras. In February 2019, WTA legends Chris Evert and Lindsay Davenport said Djokovic will break the record for most grand slam titles won in history.

He met his future wife, Jelena Ristić, in high school, and began dating her in 2005. The two became engaged in September 2013, and on 10 July 2014 the couple got married on Sveti Stefan in Montenegro, while a church wedding was held in the same place, on 12 July 2014, in the Church of Saint Stephen (Serbian: Црква Светог Архиђакона Стефана ) which belongs to Praskvica Monastery. On 24 April 2014, Djokovic announced that he and Ristić were expecting their first child. Their son, Stefan, was born on 21 October 2014 in Nice, France. Their daughter, Tara, was born on 2 September 2017.

Djokovic also would play in the Dubai Tennis Championships but lost to eventual champion Roger Federer in the semi-finals. However, Djokovic would avenge his loss to Federer, winning his third Indian Wells Masters title, beating Federer in the final. Continuing his good run, he beat No. 1 Nadal in the final of the Miami Masters in straight sets. Suffering from a wrist injury which hampered him throughout the Monte-Carlo Masters, Djokovic lost the semi-finals to Federer in straight sets. After returning from injury, Djokovic won his third Rome title by beating Nadal in the final of the Italian Open. He subsequently donated the $500,000 in prize money that he had received to the victims of the 2014 Southeast Europe floods.

During the 2014 Balkans floods, he sparked worldwide financial and media support for victims in Bosnia and Herzegovina, Croatia and Serbia. After winning the 2014 Rome Masters, Djokovic donated his prize money to the flood victims in Serbia, while his foundation collected another $600,000. Following his 2016 Australian Open victory, Djokovic donated $20,000 to Melbourne City Mission's early childhood education programm to help disadvantaged children. After the COVID-19 pandemic spread to Serbia in March 2020, he and his wife announced that they will donate €1 million for the purchase of ventilators and medical equipment to support hospitals and other medical institutions. He also made a donation to Bergamo, one of the worst-affected province.

Djokovic started the year by playing the Hopman Cup with fellow Serbian world No. 3 Jelena Janković. While he won all his round-robin matches, the team lost 1–2 in the final to the second-seeded American team of Serena Williams and Mardy Fish. At the Australian Open, Djokovic reached his second consecutive Grand Slam final without dropping a set, including a victory over two-time defending champion Federer in the semi-finals. By reaching the semi-finals, Djokovic became the youngest player to have reached the semi-finals in all four Grand Slam events. In the final, Djokovic defeated unseeded Frenchman Jo-Wilfried Tsonga in four sets to earn his first Grand Slam singles title. This marked the first time since the 2005 Australian Open that a Grand Slam singles title was not won by Federer or Nadal.

Djokovic then took part in Serbia's Davis Cup tie against the United States on clay in Belgrade and helped his country reach its first quarterfinal in the Davis Cup with a 3–2 victory, defeating Querrey and Isner. At the Indian Wells Masters, Djokovic lost in the fourth round to Ljubičić. At the Miami Masters, he lost in his opening match to Olivier Rochus. Djokovic then announced that he had ceased working with Todd Martin as his coach.

As the third seed at the US Open, Djokovic came very close to losing in his opening round against Viktor Troicki in extreme heat. He then defeated Philipp Petzschner, James Blake, Mardy Fish, and No. 17 seed Gaël Monfils, all in straight sets, to reach the US Open semi-finals for the fourth consecutive year. There, he defeated Federer in five sets after saving two match points with forehand winners while serving to stay in the match at 4–5 in the 5th set. It was Djokovic's first victory over Federer at the US Open in four attempts, and his first victory over Federer in a Major since the 2008 Australian Open. Djokovic went on to lose to Nadal in the final, a match that saw Nadal complete his career Grand Slam.

After helping Serbia defeat the Czech Republic 3–2 to make it to the Davis Cup final, Djokovic competed at the China Open as the top seed and defending champion. He won the title for the second successive year, after defeating Maoxin Gong, Mardy Fish (walkover), Gilles Simon, and John Isner en route to the final. Djokovic then defeated Ferrer in the final. At the Shanghai Masters, Djokovic made a semi-final appearance, losing to Federer. Djokovic played his final tournament of the year at the ATP World Tour Finals in London. Djokovic was placed in Group A along with Nadal, Berdych, and Roddick. Djokovic won his first round-robin match against Berdych. He next lost to Nadal. He defeated Roddick in his final round-robin match and advanced to the semi-finals, where he lost to Federer in two sets.

Serbia progressed to the Davis Cup final, following the victories over Croatia (4–1) and the Czech Republic (3–2). Serbia came from 1–2 down to defeat France in the final tie 3–2 in Belgrade to win the nation's first Davis Cup Championship. In the final, Djokovic scored two singles points for Serbia, defeating Gilles Simon and Gaël Monfils. He was the backbone of the Serbian squad, going 7–0 in singles rubbers to lead the nation to the title, although the honour of winning the deciding rubber in the final went to compatriot Viktor Troicki.

Djokovic began the 2013 season by defeating Murray in the final of the 2013 Australian Open to win a record third consecutive Australian Open trophy and the sixth major of his career. A week later, he participated in a Davis Cup match against Belgium, where he defeated Olivier Rochus in straight sets to give the Serbian team a 2–0 lead.

On 2 March 2013, Djokovic won the thirty-sixth professional single's title of his career by defeating Tomáš Berdych in the final of the Dubai Tennis Championships. Another solid week of tennis saw Djokovic reach the semi-finals at the BNP Paribas Open in Indian Wells, before losing to del Potro, bringing an end to his twenty-two match winning streak. The following week, Djokovic went into the Miami Masters as defending champion, but lost in the fourth round to Tommy Haas in straight sets.

In the finals of the 2013 Wimbledon Championships, Djokovic lost to Murray in straight sets. At the Rogers Cup, he lost to Nadal in the semi-final in three sets. Later, Djokovic lost to Isner in the quarterfinals in Cincinnati. Djokovic went on to reach the US Open final, where he met Nadal for the 37th time in his career (a new open era record). He went on to lose in four sets. In early October, Djokovic collected his fourth Beijing title by defeating Nadal in the final in straight sets. He also collected his second Shanghai Rolex Masters title, extending his winning streak to 20–0 over the last 2 seasons at the hard court Asian swing of the tour. Djokovic won his 16 Masters 1000 title in Paris at the end of the season, beating David Ferrer in the final. At the 2013 ATP World Tour Finals Djokovic retained the trophy, beating Nadal in straight sets. At the end of the season, Boris Becker joined his staff as head coach.

Djokovic began the year with a warmup tournament win, the 2013 Mubadala World Tennis Championship. At the Australian Open, he won his first four matches in straight sets, against Lukáš Lacko, Leonardo Mayer, Denis Istomin and No. 15 seed Fabio Fognini respectively. He met Wawrinka in the quarterfinals of the tournament, the second consecutive year the two had met at the event. Despite coming back from two sets to one down, Djokovic fell 9–7 in the fifth set, ending his 25–match winning streak in Melbourne, as well as his streak of 14 consecutive Grand Slam tournament semi-finals. The week of 27 January marked the first time since 2011 that Djokovic has not been a Grand Slam title holder.

He continued his good form on clay at the French Open, by reaching the final without dropping a set in the first five rounds, including a quarterfinal clash with Nadal and a five set semi-final victory over No. 3 seed Andy Murray which took two days to complete. This meant he became only the second man to have won against Nadal at the French Open. However, he lost the next match and the tournament to No. 8 seed Stan Wawrinka in four sets, after having prevailed in the first set and being up a break in the fourth set and up 40–0 on Wawrinka's serve in a subsequent game. He lost six of the final seven games of the match. With this loss, Djokovic was denied his first victory at the French Open and a personal career Grand Slam. Five weeks later, he rebounded again from a tough loss in Paris, just like 2014, coming from two sets down to beat Kevin Anderson in the fourth round, and then going on to claim his third Wimbledon title in his fourth final at the All England Club, with a four set win over Roger Federer.

He returned to Beijing in October, winning the title for the sixth time, defeating Nadal in straight sets in the final to bring his overall record at the tournament to 29–0. Djokovic then reached the final of the Paris Masters, where he defeated Murray in straight sets, taking his fourth title there and a record sixth ATP Masters 1000 tournament in one year. After losing to Federer in the round-robin stage of the 2015 ATP World Tour Finals he took on the third seed again in the final. He beat Federer in straight sets winning his fifth World Tour Finals title and he became the first player to win four consecutive end-of-year finals tournaments.

Reuniting with Marián Vajda, at the Monte Carlo Masters, he collected victories over Dusan Lajovic and Borna Coric, followed by a loss to world no. 7 Dominic Thiem. In a press conference, he stated, "After two years finally I can play without pain." After another early exit, this time in Barcelona to Martin Klizan, Djokovic's gradual return to form would show itself at the Madrid Masters. In his first win over a top 20 player in 10 months, he defeated Monte Carlo Masters runner-up Kei Nishikori in straight sets, but did not progress past the second round, losing to Kyle Edmund in three sets. Going into the Rome Masters with a 6–6 season record, he reached the semifinals, losing to Rafael Nadal in straight sets. He later reached the quarterfinals of the 2018 French Open, where he lost to Marco Cecchinato in four sets.

Djokovic entered Wimbledon as the #12 seed. He defeated Tennys Sandgren, Horacio Zeballos, Kyle Edmund, Karen Khachanov, and Kei Nishikori to reach the semifinals, where he faced long-time rival Rafael Nadal. Djokovic defeated Nadal 10–8 in the fifth set in a 5-hour, 17-minute match, spread over two days. This match became the second-longest semifinal in Wimbledon history, second only to the match between Kevin Anderson and John Isner held earlier on the same day. With this win, Djokovic reached his first major final since the 2016 US Open. He claimed his fourth Wimbledon title and 13th major title overall by defeating Anderson in straight sets after 2 hours and 18 minutes, winning the third set in a tiebreak after saving five set points throughout the set. With this win, he rose 11 ranking spots and re-entered the top 10 for the first time since October 2017.

Novak Djokovic and Rafael Nadal have met 55 times on the tennis court, an Open Era record for head-to-head meetings between male players, and Djokovic leads 29–26. Djokovic leads on hard courts 20–7, while Nadal leads on clay 17–7, and they are tied on grass 2–2. This rivalry is listed as the third greatest rivalry in the last decade by ATPworldtour.com. Djokovic is the first player to have at least ten match wins against Nadal and the only person to defeat Nadal seven times consecutively (which he did twice). The two share the record for the longest Grand Slam final match ever played (5 hours and 53 minutes), which was the 2012 Australian Open final.

In 2013, Djokovic defeated Nadal in straight sets in the final of the Monte-Carlo Masters to clinch his first title in Monte Carlo. This was his third clay win against Nadal. At the 2013 French Open semifinal, Nadal defeated Djokovic to up his record to 20–15 against Djokovic, and again at the 2013 Rogers Cup semifinal. On 9 September 2013, Djokovic lost to Nadal in the 2013 US Open final in four sets. In 2014, Djokovic defeated Nadal in 3 sets at the Rome Masters 1000 tournament to claim his 3rd title there. At the 2014 French Open, they played in the final, with Djokovic again attempting to capture the Career Grand Slam. Nadal won in four sets to capture the French Open for the ninth time.

Novak Djokovic and Roger Federer have faced each other 50 times (not including one occasion when there was a walkover in favour of Djokovic), and Djokovic currently leads 27–23. Djokovic leads on hard courts 20–18 as well as grass 3–1, whereas they are split 4–4 on clay. Djokovic is the only player other than Nadal who has defeated Federer in consecutive Grand Slam tournament matches. Federer ended Djokovic's 41-match winning start to the 2011 season at the 2011 French Open semi-finals. However, Federer would lose to Djokovic in the following year in straight sets. Djokovic played Federer in his first Major final at the 2007 US Open and lost in three sets.

Djokovic and Andy Murray have met 36 times with Djokovic leading 25–11. Djokovic leads 5–1 on clay, 20–8 on hard courts, and Murray leads 2–0 on grass. The two are almost exactly the same age, with Murray being a week older than Djokovic. They went to training camp together, and Murray won the first match they ever played as teenagers. The pair have met 19 times in finals, and Djokovic leads 11–8. Ten of the finals were ATP Masters 1000 finals, and they are tied at 5–5. Their most notable match in this category was a three set thriller at the final of the 2012 Shanghai Masters, in which Murray held five championship point opportunities in the second set; however, Djokovic saved each of them, forcing a deciding set. He eventually prevailed to win his first Shanghai Masters title, ending Murray's 12–0 winning streak at the event. This, and the three set match they played in Rome in 2011, were voted the ATP World Tour match of the Year, for each respective season. They have also met in seven Grand Slam tournament finals: The 2011 Australian Open, the 2012 US Open, the 2013 Australian Open, the 2013 Wimbledon Championships, the 2015 Australian Open, the 2016 Australian Open and most recently, the 2016 French Open. Djokovic has won in Australia four times and won at the French Open, while it was Murray who emerged the victor at the US Open and Wimbledon.

Djokovic and Stan Wawrinka have met 25 times with Djokovic leading 19–6, however the two have contested numerous close matches, including four five-setters at Grand Slam level. Wawrinka and Djokovic have played three consecutive Australian Open years, each match going to five sets, and a five-setter in the US Open: in the 2013 Australian Open fourth round, which Djokovic won 12–10 in a fifth set; at the 2013 US Open semi-finals, which Djokovic won 6–4 in a fifth set; and at the 2014 Australian Open quarterfinals, which Wawrinka won 9–7 in a close fifth set. Wawrinka's win broke Djokovic's impressive run of 14 consecutive semi-finals in Grand Slam play, ended a 28-match winning streak, and prevented Djokovic from capturing a record fifth Australian Open crown. Djokovic got revenge in the 2015 Australian Open, winning 6–0 in the fifth set, but again it went the distance. At the 2015 French Open final, Wawrinka defeated Djokovic in four sets to claim his second major title. In 2015, Djokovic defeated Wawrinka at the Paris Masters. At the 2016 US Open, Wawrinka beat Djokovic in a Grand Slam final for the second time. Suffering from a foot injury for the latter stages of the match, Djokovic lost in four sets. He did not attribute his loss to the injury, but rather to Wawrinka's courageous play at decisive moments in the match. Contrary to most high-profile rivalries, they have played doubles together.

Despite Djokovic's 19–6 overall record against Wawrinka, Wawrinka leads Djokovic 2–0 in Grand Slam finals and 3–2 in all ATP finals. During Djokovic's run of eight appearances at Grand Slam finals from 2014 Wimbledon through the 2016 US Open, his only two losses came at the hands of Wawrinka. Moreover, in Djokovic's 21 Grand Slam championship matches, Wawrinka is the only opponent he has not defeated and the only opponent outside the Big Four who has defeated him.

Djokovic and Jo-Wilfried Tsonga have met 24 times with Djokovic leading 18–6. Their first meeting was in the final of the 2008 Australian Open; Djokovic and Tsonga had defeated the top two players, Roger Federer and Rafael Nadal in their respective semi-finals in straight sets. Djokovic won this match in 4 sets to win his first Grand Slam singles title.

Djokovic and Juan Martín del Potro have met 20 times with Djokovic leading 16–4. Djokovic won their first four meetings, before back to back victories for del Potro at the 2011 Davis Cup and their Bronze medal match at the 2012 Summer Olympics in straight sets. However, in 2013, Djokovic got the upper hand on the rivalry again and won two of the most important matches between them to date; an epic five-setter at the 2013 Wimbledon Championships semifinals which was the longest Wimbledon semifinal at the time, and a thrilling three-setter at the 2013 Shanghai Masters final. In the same year, del Potro defeated Djokovic en route to his second Masters 1000 final, at the 2013 Indian Wells Masters, where he lost to Nadal. Del Potro upset Djokovic in the first round at the 2016 Olympics in Rio en route to the final, where he lost to Murray. Djokovic defeated del Potro in three close sets in the final of the 2018 US Open, which was the first grand slam final for del Potro since his victory at the 2009 US Open.

Djokovic began his season by winning the 2012 Australian Open. He won his first four rounds against Paolo Lorenzi, Santiago Giraldo, Nicolas Mahut and Lleyton Hewitt, respectively. In the quarterfinals he defeated David Ferrer in three sets. In the semi-final, Djokovic beat Murray in five sets after 4 hours and 50 minutes, coming back from a two-sets-to-one deficit and fending off break points at 5-all in the fifth set. In the final, Djokovic beat Nadal in five sets, coming from a break down in the final set to win 7–5. At 5 hours and 53 minutes, the match was the longest final in Open Era Grand Slam history, as well as the longest match in Australian Open history, surpassing the 5-hour and 14-minute 2009 semi-final between Nadal and Fernando Verdasco.

Djokovic was beaten by John Isner in the semi-finals at Indian Wells. He successfully defended his title in Miami. In the Monte Carlo final, he lost in straight sets to Nadal, unable to prevent Nadal from earning his record-breaking eighth consecutive title there. Djokovic also lost in straight sets to Nadal at the Rome Masters 2012 final.

Djokovic reached his maiden French Open final in 2012 by defeating Federer, reaching the finals of all four majors consecutively. Djokovic had the chance to become the first man since Rod Laver in 1969 to hold all four major titles at once, having won last year's Wimbledon and US Open titles as well as this year's Australian Open, but was beaten by Nadal in the final in four sets. Following the French Open, Djokovic was unsuccessful in defending his Wimbledon title from the prior year, losing to Roger Federer in four sets in the semi-finals.

At the 2012 Summer Olympics in London, Djokovic was chosen as the flag bearer for Serbia. On 2 August 2012, Djokovic defeated French fifth seed Tsonga and advanced to the semi-finals of Olympics, where he was beaten by Murray in straight sets. In the bronze medal match he lost to Del Potro, finishing 4th. He successively defended his Rogers Cup title, dropping just a single set to Tommy Haas. Following the Rogers Cup, Djokovic would make the finals of the Cincinnati Masters but lost to Roger Federer in straight sets.

At the US Open on 9 September, Djokovic reached his third consecutive final at Flushing Meadows by beating fourth-seeded David Ferrer in a match suspended a day earlier due to rain. He then lost the final to Murray in five sets. Djokovic went on to defend his China Open title, defeating Tsonga in straight sets. The following week he won the Shanghai Masters by defeating Murray in the final. With Federer's withdrawal from the Paris Masters, Djokovic was guaranteed to regain his No. 1 ranking. On 12 November 2012, Djokovic won the 2012 ATP World Tour Finals by defeating Federer in the final. Because of his achievements in the 2012 season, Djokovic was named the 2012 ITF World Champion in men's singles by the International Tennis Federation.

At the 2012 Monte-Carlo Rolex Masters in April, Nadal finally beat Djokovic for the first time since November 2010. They had met in seven finals from January 2011 to January 2012, all of which Djokovic won. Nadal again defeated Djokovic in the final of the Rome Masters tournament.

At the 2012 French Open, Djokovic faced Nadal in the final. For the second time in tennis history, two tennis players played four consecutive Grand Slams finals against each other. They also became the only players in history, except for Venus and Serena Williams, to have faced the same opponent in the finals of each of the four different Grand Slam events. Nadal eventually won in four sets after multiple rain delays that forced the final to be concluded on the following Monday afternoon.

Djokovic and Murray also played an almost five-hour-long semi-final match in the 2012 Australian Open, which Djokovic won 7–5 in the fifth set after Murray led two sets to one. Murray and Djokovic met again in 2012 at the London 2012 Olympic Games, with Murray winning in straight sets. The two met in the final of the 2013 Wimbledon Championships, where second seed Murray defeated Djokovic in straight sets, the first time since 2010 that Djokovic had failed to win a set in a Grand Slam match. In the final of the 2015 Paris Masters, Djokovic triumphed in two sets and became the first man to win six Masters tournaments in one season. At the 2016 Australian Open final, in a rematch of the previous final, Djokovic won in three sets and captured his sixth Australian Open title.

They met again two months later at the Olympics, with Djokovic winning in straight sets in the quarterfinals. They met in the final of the 2012 China Open, with Djokovic once again victorious in straight sets. The pair were drawn in the same pool for the 2012 ATP World Tour Finals. Djokovic defeated Tsonga in his first (of three) round robin matches. It was Djokovic's fifth win over Tsonga in 2012.

Tennis pundits have classified many of Djokovic's matches as some of the greatest contests ever, with the 2012 Australian Open final being considered one of the greatest matches ever seen. Some longtime analysts claim that the Djokovic–Nadal rivalry ranks as the best rivalry in tennis history primarily because of the quality of matches they produce.

Djokovic commented on the modern style of play, including his own, in interview with Jim Courier after his semi-final win against Andy Murray in the 2012 Australian Open tournament:

From 2011, Djokovic began to wear custom Red and Blue Adidas Barricade 6.0's shoes, referring to the colours of the Serbian national flag. By April 2012, the Tacchini deal had fallen first short and then apart. At that point, he was set to join forces with Nike, Inc., but instead, on 23 May 2012, Uniqlo appointed Djokovic as its global brand ambassador. The five-year sponsorship, reportedly worth €8 million per year, began on 27 May 2012 in Paris' Roland-Garros French Open Tennis Tournament. A year later, Djokovic's long-term footwear deal with Adidas was announced ahead of 2013 French Open.

He appeared on the cover of Italian GQ's March 2012 issue. Also, in March he was profiled on the CBS show 60 Minutes by their correspondent Bob Simon. He was named amongst the 100 most influential people of 2012 by TIME magazine.

Djokovic is the first Serbian player to be ranked No. 1 by the ATP and the first male player representing Serbia to win a Grand Slam singles title. He is a six-time ITF World Champion and a five-time ATP year-end No. 1 ranked player. Djokovic has won numerous awards, including the Laureus World Sports Award for Sportsman of the Year (four times) and the 2011 BBC Overseas Sports Personality of the Year award. He is also a recipient of the Order of St. Sava, the Order of Karađorđe's Star, and the Order of the Republika Srpska.

Djokovic is a member of the Serbian Orthodox Church. On 28 April 2011, Patriarch Irinej of Serbia awarded Djokovic the Order of St. Sava I class, the highest decoration of the Serbian Orthodox Church, for his contributions to monasteries of the Serbian Orthodox Church in Kosovo and Metohija and charitable work in Serbia. He is a keen fan of Serbian football club Red Star Belgrade, Italian club A.C. Milan and Portuguese club S.L. Benfica. He is good friends with fellow Serbian tennis player Ana Ivanovic, whom he has known since the two were children growing up in Serbia, through Djokovic's uncle and Ivanovic's father.

Djokovic went on to win his two singles rubbers in Serbia's Davis Cup finals victory over France. This started a long unbeaten run that went on into 2011. Djokovic finished the year ranked No. 3, his fourth successive finish at this position. He was awarded the title "Serbian Sportsman of the year" by the Olympic Committee of Serbia and "Serbian Athlete of the year" by DSL Sport.

Djokovic won ten tournaments in 2011, including Grand Slam tournament victories at the Australian Open, Wimbledon and the US Open. Djokovic also captured a record-breaking five ATP World Tour Masters 1000 titles, and set a new record for the most prize money won in a single season on the ATP World Tour ($12 million). His level dropped at season's end beginning with a back injury and ended with a poor showing at the ATP World Tour Finals. Djokovic finished the season with a 70–6 record and a year-end ranking of No. 1.

Pete Sampras declared Djokovic's 2011 season as the best he has ever seen in his lifetime, calling it "one of the best achievements in all of sports." Boris Becker called Djokovic's season "one of the very best years in tennis of all time", adding that it "may not be the best statistically, but he's beaten Federer, he's beaten Nadal, he's beaten everybody that came around to challenge him in the biggest tournaments in the world." Rafael Nadal, who lost to Djokovic in six finals on three different surfaces, described Djokovic's performances as "probably the highest level of tennis that I ever saw." Djokovic was named 2011 ITF World Champion. He also received the Golden Bagel Award by winning 13 sets with the result of 6–0 during the season.

In the semi-finals of the 2011 Davis Cup, Djokovic played a crucial rubber match for Serbia against Juan Martín del Potro of Argentina, where he retired while trailing, after reaggravating a back injury sustained during the US Open tournament. This secured Argentina's place in the final. This marked Djokovic's third loss of his 2011 season, and his second retirement.

In the 2011 Wimbledon final, Djokovic won in four sets, which was his first victory over Nadal in a Major. By doing so, he became the only person other than Federer to defeat Nadal in a Grand Slam tournament final. Djokovic also defeated Nadal in the 2011 US Open Final to capture his third major title of the year and fourth overall. By beating Nadal, Djokovic became the second player to defeat Nadal in more than one Grand Slam final (the other being Federer), and the first player to beat Nadal in a Slam final on a surface other than grass. In 2012, Djokovic defeated Nadal in the Australian Open final which made Nadal the first player to lose in three consecutive Grand Slam finals.

Djokovic is considered to be one of the greatest tennis players of all time. Following his tremendous success in the 2011 season, he began to feature on all-time greatest lists and, in late 2011, Rod Laver listed Djokovic number six in his top ten male players of the Open Era. According to Tim Henman's June 2012 statement, Djokovic is "probably a top eight player in tennis history". Andre Agassi stated in September 2012 that Federer, Nadal, and Djokovic "may very well be the greatest three players to ever play tennis". In March 2012, contemporary competitor Andy Murray described Djokovic as 'one of the greatest players ever'. Following the 2013 US Open, in his September 2013 men's greatest players of all-time list, International Business Times' writer Jason Le Miere put the then six-time Grand Slam-winning Serb in seventh place, behind Federer, Nadal, Sampras, Laver, Borg, and Agassi. In January 2014, ESPN writer Howard Bryant called him 'arguably the best pure tennis player in the world'.

In assessing Djokovic's 2011 season, Jimmy Connors said that Djokovic gives his opponents problems by playing "a little bit old-school, taking the ball earlier, catching the ball on the rise, (and) driving the ball flat." Connors adds that a lot of the topspin that Djokovic's opponents drive at him comes right into his zone, thus his ability to turn defense into offense well.

After retiring from professional tennis in August 2011, Serbian player Dušan Vemić joined Djokovic's team as assistant coach and hitting partner for Novak. The collaboration ended before the 2013 US Open.

In August 2011, Djokovic became the brand ambassador of Swiss watch manufacturer Audemars Piguet. Less than a month later, Djokovic signed a sponsorship deal with German car company Mercedes-Benz. In March 2012, Djokovic was announced by Bombardier Aerospace as its latest Learjet brand ambassador, thus joining the likes of actor and pilot John Travolta, architect Frank Gehry, maestro Valery Gergiev, and classical pianist Lang Lang. From January 2014 Djokovic has been endorsing French car manufacturer Peugeot. At the same time he entered into an endorsement deal with Japanese watch manufacturer Seiko, having just ended his affiliation with their rivals Audemars Piguet. In early 2015, ahead of the Australian Open, Djokovic teamed up with Australian banking corporation ANZ for a social media campaign to raise money for local communities across the Asia Pacific region. At the same time his partnership with Jacob's Creek, an Australian wine brand owned by Orlando Wines, was announced in regards to the production and distribution of 'Made By' film series, a documentary style content meant to "show a side of Novak not seen before as he recounts never before told life stories from Belgrade, Serbia, celebrating what has made him the champion he is today".

The company launched Novak Café & Restaurant in 2008 in the Belgrade municipality of Novi Beograd, the flagship location in a franchised chain of theme café-restaurants. During 2009, two more locations were added—one in Kragujevac and the other in Belgrade, the city's second, in September at the neighbourhood of Dorćol overlooking the playing courts of Serbia Open whose inaugural edition took place several months earlier. On 16 December 2011 a location in Novi Sad was opened, however, it operated just over three years before closing in late March 2015. Banja Luka in neighbouring Republika Srpska got its Novak Café & Restaurant location on 16 October 2015 within Hotel Trešnja on Banj hill.

On 25 June 2011, at the Serbian National Defense Council's seventieth congress in Chicago, Djokovic was unanimously awarded the Order of Serbian National Defense in America I class — the highest decoration of the SND. The order was given to the twenty-four-year-old for his merits on the international sport scene and his contributions to the reputation of Serbs and Serbia around the world. The day after winning his first Wimbledon title and reaching the No. 1 ranking for the first time in his career, Djokovic went home to Belgrade for a homecoming celebration in front of the Serbian National Assembly, an event attended by close to 100,000 people.

On 28 November 2011, after returning from London where he finished early due to failing to progress out of his round-robin group, Djokovic visited his childhood tennis coach Jelena Genčić at her Belgrade home, bringing the Wimbledon trophy along. The meeting, reportedly their first in more than four years, was recorded by two television crews — a Serbian one shooting for Aleksandar Gajšek's show Agape on Studio B television and an American one from CBS television network filming material for Djokovic's upcoming piece on 60 Minutes. The next day, 29 November 2011, on invitation from film producer Avi Lerner, Djokovic was part of the high-budget Hollywood movie production The Expendables 2 in a cameo playing himself that was shot in a warehouse in the Bulgarian capital of Sofia. However, his bit part was later cut out of the final version of the movie.

Note: Djokovic's quarterfinal match at the 2011 French Open and his second round match at the 2016 US Open were walkovers (so not counted as wins)

During the US Open Series, Djokovic made the quarterfinals of the Rogers Cup in Montreal before losing to Roddick. At the Cincinnati Masters, Djokovic defeated third-ranked Nadal in the semi-finals before losing in the final to No. 1 Federer. At the US Open, Djokovic made the semi-finals, having dropped only two sets, defeating Ivan Ljubičić, 15th seed Radek Štěpánek and 10th seed Fernando Verdasco before being defeated by Federer.

Djokovic ended the year as the No. 3 for the third consecutive year, having played 97 matches, the most of any player on the ATP World Tour, with a 78–19 win-loss record. In addition to leading the ATP World Tour in match wins, he reached a career best ten finals, winning five titles. Djokovic also played a large role in promoting Serbia to the 2009 World Group. On 6–8 March 2010, he played a key role in bringing Serbia to the World Group quarterfinals for the first time in its independent history, winning both singles matches in the home tie against the United States against Sam Querrey and John Isner.

Djokovic started his year by playing in the AAMI Classic, an exhibition event. In his first match, he defeated Haas before losing to Fernando Verdasco in his second. At the 2010 Australian Open, Djokovic lost a five-setter to Tsonga in the quarterfinals. Despite the loss, he attained a career-high ranking of No. 2 and went on to reach the semi-finals of the ABN AMRO World Tennis Tournament in Rotterdam, where he lost to Youzhny. At the Dubai Tennis Championships, Djokovic reached the final, this time defeating Youzhny to win his first title of the year.

Their next meeting at a Grand Slam event was again at the Australian Open, in the 2010 quarterfinals, exactly two years to the day since Djokovic defeated Tsonga to win his first Grand Slam singles title. However, this time it was Tsonga who prevailed, winning in five sets after Djokovic fell ill during the match. It would be another year-and-a-half until they met again, with the stakes even higher – in the semi-finals at Wimbledon in 2011, with the winner advancing to his first Wimbledon final. It was their first meeting on grass, and Djokovic prevailed in four sets to advance to his first Wimbledon final, and in the process ending the seven-and-a-half-year reign of Roger Federer and Rafael Nadal at the top of the rankings. At the 2012 French Open, Djokovic and Tsonga met again in an important quarterfinals match, with Djokovic prevailing in five sets after more than four hours of play.

In July 2010, before the Davis Cup clash away at Croatia, Djokovic made another addition to his team – nutritionist Igor Četojević who additionally focuses on Chinese medicine and does acupuncture. He allegedly discovered that the tennis player suffers from gluten intolerance, using applied kinesiology, and that he cannot eat gluten, purging it from his diet. It appeared to have worked as Djokovic began feeling stronger, quicker, and much more fit. He eventually settled on a vegan diet. He later added the occasional consumption of fish to his dietary regimen. After Djokovic's Wimbledon win in July 2011, Četojević left the team. A Wall Street Journal article noted, "He had an otherworldly season in 2011 and has been the world's most consistent player since. His devotion to his diet has only gotten stronger. (In 2016) he opened a vegan restaurant in Monte Carlo, where he lives."

He participated in charity matches with the aim of raising funds for the reconstruction of the Avala Tower, as well as to aid victims of the 2010 Haiti earthquake and 2010–11 Queensland floods. Djokovic was selected as the 2012 Arthur Ashe Humanitarian of the Year, for his contributions through the foundation, his role as a UNICEF national ambassador and other charitable projects. In August 2015, he was appointed a UNICEF Goodwill Ambassador.

Djokovic is also featured in the music video for the song "Hello" by Martin Solveig and Dragonette. The video, filmed at Stade Roland Garros, shows Solveig facing off against Bob Sinclar, another DJ, in a tennis match. When the referee calls a crucial ball "Out", Djokovic enters the arena and convinces the referee otherwise. In 2010, the Serbian blues-rock band Zona B recorded the song "The Joker", dedicating it to Djokovic.

Djokovic is an aggressive baseline player. His groundstrokes from both wings are consistent, deep, and penetrating. His backhand is widely regarded as one of the best in today's game, due to its effectiveness on both sides of the court. His best shot is his backhand down the line, with great pace and precision. He is also known as one of the greatest movers on the court with high agility, court coverage and defensive ability, which allows him to hit winners from seemingly defensive positions. After great technical difficulties during the 2009 season (coinciding with his switch to the Head racket series), his serve is one of his major weapons again, winning him many free points; his first serve is typically hit flat, while he prefers to slice and kick his second serves wide.

In 2009, the company bought a 250-series ATP tournament known as the Dutch Open and moved it to Serbia where it was renamed the Serbia Open. With the help of Belgrade city authorities, the tournament's inaugural edition was held during May 2009 at the city-owned 'Milan Gale Muškatirović' courts, located at an attractive spot in Dorćol neighbourhood. The tournament folded in 2012 after four editions and its place in the ATP calendar got taken over by the Düsseldorf Open.

Throughout late April and early May 2009, during ATP Master Series tournaments in Rome and Madrid, respectively, the Serb was a guest on the Fiorello Show on Sky Uno hosted by Italian comedian Rosario Fiorello followed by an appearance on Pablo Motos' show El Hormiguero. In 2009, and 2010, Djokovic won an Oscar of Popularity for the most popular male athlete in Serbia.

Djokovic entered the Australian Open as the top seed. He defeated qualifier Mitchell Krueger, 2008 finalist Jo-Wilfried Tsonga, 25th seed Denis Shapovalov, 15th seed Daniil Medvedev, 8th seed Kei Nishikori, and 28th seed Lucas Pouille to reach the final, in which he beat 2nd seed Rafael Nadal in straight sets to win his 15th Grand Slam and a record 7th Australian Open. Djokovic then played at the 2019 Indian Wells Masters and reached the third round where he was upset by Philipp Kohlschreiber in straight sets. This was then followed by a three-set fourth round defeat to Roberto Bautista Agut in the 2019 Miami Open. Djokovic then began his clay court season by playing in the 2019 Monte Carlo Masters, losing in the quarterfinals to Daniil Medvedev in three sets.

Djokovic's return of serve is a powerful weapon for him, with which he can be both offensive and defensive. Djokovic is rarely aced because of his flexibility, length and balance. Djokovic is highly efficient off both the forehand and backhand return, often getting the return in play deep with pace, neutralizing the advantage the server usually has in a point. John McEnroe considers Djokovic to be the greatest returner of serve in the history of the men's game. Occasionally, Djokovic employs a well-disguised backhand underspin drop shot and sliced backhand. His smash is considered to be one of his biggest weaknesses, being prone to making mistakes on the shot in big moments such as the 2008 Olympics.

Djokovic began 2007 by defeating Australian Chris Guccione in the final of the tournament in Adelaide, before losing in the fourth round of the Australian Open to eventual champion Roger Federer in straight sets. His performances at the Masters Series events in Indian Wells, and Key Biscayne, where he was the runner-up and champion respectively, pushed him into the world's top 10. Djokovic lost the Indian Wells final to Rafael Nadal, but defeated Nadal in Key Biscayne in the quarterfinals before defeating Guillermo Cañas for the title in the finals.

Djokovic played a key role in the 2007 play-off win over Australia by winning all his matches and helping promote the Serbia Davis Cup team to the 2008 World Group. In Serbia's tie against Russia in Moscow in early 2008, Djokovic was sidelined due to influenza and missed his first singles match. He returned to win his doubles match, teaming with Nenad Zimonjić, before retiring during his singles match with Nikolay Davydenko.

Djokovic then failed to defend his 2007 singles title at the Rogers Cup in Toronto – he was eliminated in the quarterfinals by eighth-seeded Andy Murray. The following week at the Cincinnati Masters, Djokovic advanced to the final, beating Nadal in the semifinals and thereby ending the Spaniard's 32 match winning streak. In the final, he again lost to Murray in straight sets. His next tournament was the 2008 Summer Olympics, his first Olympics. He and Nenad Zimonjić, seeded second in men's doubles, were eliminated in the first round by the Czech pairing of Martin Damm and Pavel Vízner. Seeded third in singles, Djokovic lost in the semi-finals to Nadal. Djokovic then defeated James Blake, the loser of the other semi-final, in the bronze medal match.

Djokovic has more wins against Federer than any other player. The two had three encounters at the Australian Open (in 2007, 2008, and 2011), which Federer won in straight sets in 2007 and Djokovic won in straight sets in the other two. The two have met five years in a row at the US Open with Federer triumphant in their first three encounters, while their last two meetings (in 2010 and 2011) were five-set matches in which Djokovic saved two match points before going on to win. In 2012, Djokovic lost to Federer in the Wimbledon semi-final. Djokovic won the 2012 ATP World Tour Finals by defeating Federer in straight sets in the final. The two met again during the finals of the 2014 Wimbledon Championships with Djokovic emerging victorious after a five-set match and with the victory reclaiming the No. 1 ranking from Nadal. Federer withdrew from the 2014 ATP World Tour final and Djokovic successfully defended his title, the first walkover in a final in the tournament's 45-year history. In the 2015 Wimbledon Championships, despite "an extraordinary second-set tiebreaker in which Federer saved seven set points to level the match", Djokovic went on to claim a four set victory and even the lifetime record between the two players. The two met again in another Grand Slam final in 2015, this time at the 2015 US Open, where Djokovic defeated Federer in four tight sets to claim his second US Open title and tenth Grand Slam.

In 2007, Djokovic founded the Novak Djokovic Foundation. The organization's mission is to help children from disadvantaged communities to grow up and develop in stimulating and safe environments. The foundation partnered with the World Bank in August 2015 to promote early childhood education in Serbia. His foundation has built 43 schools and supported almost 20,800 children and a thousand families.

Throughout the latter part of the 2007 season, most notably before Wimbledon and during US Open, his comedic impressions of fellow contemporary tennis players got a lot of media play. It began when a BBC camera crew recorded some footage of the twenty-year-old impersonating Maria Sharapova, Rafael Nadal, Goran Ivanišević, and Lleyton Hewitt on a practice court at London's Queen's Club Championships just before Wimbledon. The material — consisting of Djokovic imitating the said players by exaggerating their trademark physical gestures or nervous tics for the entertainment of his coaching team Marián Vajda and Mark Woodforde — aired during BBC's coverage of the tournament and subsequently became popular online. Two months later at the US Open, a phone video shot by Argentine players of Djokovic doing locker room impressions of Andy Roddick, Roger Federer, Filippo Volandri, Nadal, etc. made its way online, becoming viral. A few days later, after beating Carlos Moyá in the quarterfinals, USA Network's on-court interviewer Michael Barkann asked Djokovic to perform some impressions and the player obliged by doing Sharapova and Nadal to the delight of the crowd.

In addition to Novak, the surge of popularity for tennis in the country also centered around three more up-and-coming young players: twenty-year-old Ana Ivanovic, twenty-two-year-old Jelena Janković, and twenty-three-year-old Janko Tipsarević as evidenced in early December 2007 when a sports-entertainment show named NAJJ Srbije (The Best of Serbia), put together in honour of the four players' respective successes in the 2007 season, drew a capacity crowd to Belgrade's Kombank Arena. In May 2008, he was a special guest during the first semi-final of the Eurovision Song Contest, held in Belgrade that year. He threw a big tennis ball into the crowd, announcing the start of the voting and together with one of the show's co-presenters, Željko Joksimović, Djokovic sang Đorđe Marjanović's song "Beograde".

A resident of Monte Carlo, Djokovic was coached by former Slovak tennis player Marián Vajda from 2006 until Boris Becker took over the role of head coach in December 2013. Djokovic is a self-described fan of languages, speaking Serbian, English, French, German, and Italian.

On 9 April 2006, Djokovic clinched a decisive Davis Cup win against Great Britain by defeating Greg Rusedski in four sets in the fourth match of the tie, giving Serbia and Montenegro an insurmountable 3–1 lead in their best-of-five series, thus keeping the country in the Group One Euro/African Zone of Davis Cup. Afterwards, Djokovic briefly considered moving from Serbia to play for Great Britain. Following this match-up, the British media spoke of Djokovic's camp negotiating with the Lawn Tennis Association about changing his international loyalty by joining British tennis ranks. The nineteen-year-old Djokovic, who was ranked sixty-third in the world at the time, mostly dismissed the story at first by saying that the talks were not serious, describing them as "the British being very kind to us after the Davis Cup." However, more than three years later, in October 2009, Djokovic confirmed that the talks between his family and the LTA throughout April and May 2006 were indeed serious:

From June 2006 until May 2017, Djokovic was coached by Slovakian former professional tennis player Marián Vajda. They met for the first time during that year's French Open, after which Vajda was hired to be the 19-year-old's coach. On occasion Djokovic employed additional coaches on part-time basis: in 2007, during the spring hardcourt season, he worked with Australian doubles ace Mark Woodforde with specific emphasis on volleys and net play while from August 2009 until April 2010 American Todd Martin joined the coaching team, a period marked by his ill-fated attempt to change Djokovic's serve motion. From early 2007 until 2017, Djokovic worked with physiotherapist Miljan Amanović, who was previously employed by Red Star Belgrade, and NBA player Vladimir Radmanović.

From the fall 2006, Djokovic had an Israeli fitness coach, Ronen Bega, but the two parted ways during spring 2009. Djokovic decided to make a change after identifying his conditioning as a weakness in his game following continual losses to Nadal. In April 2009, ahead of the Rome Masters, Djokovic hired Austrian Gebhard Phil-Gritsch (formerly worked with Thomas Muster) to join the team in fitness coach capacity.

Djokovic made his first Grand Slam tournament appearance by qualifying for the 2005 Australian Open, where he was defeated by eventual champion Marat Safin in the first round in straight sets, after defeating future rival Stanislas Wawrinka in qualifying. He went on to reach the third round of both Wimbledon and the US Open, coming back from two sets down to defeat Guillermo García-López in the former, and beating Gaël Monfils and Mario Ančić in the latter. Djokovic participated in four Masters events and qualified for two of them, his best performance coming in Paris, where he reached the third round and defeated fourth seed Mariano Puerta along the way.

Entering the pro circuit, Djokovic used the Head Liquidmetal Radical, but changed sponsors to Wilson in 2005. He couldn't find a Wilson racquet he liked, so Wilson agreed to make him a custom racquet to match his previous one with Head. After the 2008 season, Djokovic re-signed with Head, and debuted a new paint job of the Head YouTek Speed Pro at the 2009 Australian Open. He then switched to the Head YouTek IG Speed (18x20) paint job in 2011, and in 2013, he again updated his paint job to the Head Graphene Speed Pro, which included an extensive promotional campaign. Djokovic uses a hybrid of Head Natural Gut (gauge 16) in the mains and Luxilon Big Banger ALU Power Rough (gauge 16L) in the crosses. He also uses Head Synthetic Leather Grip as a replacement grip. In 2012, Djokovic appeared in a television commercial with Maria Sharapova promoting the use of Head rackets for many techniques such as golf and ten-pin bowling.

In 2005, as Djokovic moved up the tennis rankings, he began venturing into the business world. Most of his activities in the business arena have been channeled through Family Sport, a legal entity in Serbia established and run by members of his immediate family. Registered as a limited liability company, Family Sport initially focused on hospitality, specifically the restaurant business, by launching Novak Café & Restaurant, a franchise themed around Djokovic's tennis success. Over time, the company, whose day-to-day operations are mostly handled by Novak's father Srdjan and uncle Goran, expanded its activities into real estate, sports/entertainment event organization, and sports apparel distribution.

In the period 2004 and 2005, Djokovic was coached by Dejan Petrovic. From fall 2005 until June 2006, he was coached by Riccardo Piatti, who divided his time between the 18-year-old and Ivan Ljubičić. Player and coach reportedly parted ways over the latter's refusal to work full-time with Djokovic.

Since 2004, the business end of Djokovic's career has been handled by Israeli managers Amit Naor (former pro tennis player turned sports agent) and Allon Khakshouri, the duo that also had Marat Safin and Dinara Safina as their clients. In June 2008, after the duo entered into partnership with CAA Sports, the sports division of Hollywood talent firm Creative Artists Agency, meaning that the famous company started representing tennis players for the first time, Djokovic formally signed with CAA Sports. After Djokovic's contract with CAA Sports expired during summer 2012, he decided to switch representation, announcing IMG Worldwide as his new representatives in December 2012.

Djokovic turned professional in 2003 by entering the ATP World Tour. At the beginning of his professional career, he mainly played in Futures and Challenger tournaments, winning three of each type from 2003 to 2005. His first tour-level tournament was Umag in 2004, where he lost to Filippo Volandri in the round of 32.

Since turning professional in 2003, Djokovic has been wearing Adidas clothing. At the end of 2009, Djokovic signed a 10-year deal with the Italian clothing company Sergio Tacchini after Adidas refused to extend his clothing contract (choosing instead to sign Andy Murray). Tacchini doesn't make shoes so Djokovic continued with Adidas as his choice of footwear. His sponsorship contract with Tacchini was incentive heavy, and due to Djokovic's disproportionate success and dominance in 2011, the company fell behind on bonus payments, leading to the termination of the sponsorship contract.

As a member of the Yugoslav national team, Djokovic reached the final of the 2001 Junior Davis Cup for players under 14, in which he lost his match in singles. In juniors, Djokovic compiled a singles win/loss record of 40–11 (and 23–6 in doubles), reaching a combined junior world ranking of No. 24 in February 2004. At the junior Grand Slam tournaments his best showing was at the Australian Open where he reached the semi-finals in 2004. He also played at the French Open and US Open junior events in 2003.

Genčić worked with young Djokovic over the following six years before realizing that, due to his rapid development, going abroad in search of increased level of competition was the best option for his future. To that end, she contacted Nikola Pilić and in September 1999 the 12-year-old moved to the Pilić tennis academy in Oberschleißheim, Germany, spending four years there. At the age of 14, he began his international career, winning European championships in singles, doubles, and team competition.

Six-time major champion and former world No. 1 Boris Becker, who had mostly worked as television pundit for BBC Sport and Sky Sports since retiring from playing in 1999, was announced as Djokovic's new head coach in December 2013. According to Djokovic, the Becker appointment was done with input from the player's existing head coach Marián Vajda who reportedly wanted to spend more time with his family and was looking to have his coaching workload somewhat reduced. For Becker, in addition to working alongside Vajda, the job entailed special emphasis on Grand Slam tournaments as Djokovic felt he missed out on winning a couple of majors over the previous two seasons due to a lack of mental edge in the final stages of those tournaments. Becker's first tournament coaching Djokovic was the 2014 Australian Open.

Djokovic's next tournament was the Rogers Cup in Montreal, and he defeated No. 3 Andy Roddick in the quarterfinals, No. 2 Nadal in the semi-finals, and No. 1 Federer in the final. This was the first time a player had defeated the top three ranked players in one tournament since Boris Becker in 1994. Djokovic was also only the second player, after Tomáš Berdych, to have defeated both Federer and Nadal since they became the top two players in the world. After this tournament, Björn Borg stated that Djokovic "is definitely a contender to win a Grand Slam (tournament)." The following week at the Cincinnati Masters, Djokovic lost in the second round to Moyà in straight sets. Nevertheless, he went on to reach the final of the US Open, where he had five set points in the first set and two in the second set, but lost them all before losing the match in straight sets to the top-seeded Federer.

Djokovic began playing tennis at the age of four. In the summer of 1993, the six-year-old was spotted by Yugoslav tennis player Jelena Genčić at Mount Kopaonik, where Djokovic's parents ran a fast-food parlour. Upon seeing the child Djokovic playing tennis, she stated: "This is the greatest talent I have seen since Monica Seles."

Novak Djokovic (Serbian: Новак Ђоковић , romanized: Novak Đoković, pronounced [nôʋaːk dʑôːkoʋitɕ] ( listen ) ; born 22 May 1987) is a Serbian professional tennis player who is currently ranked world No. 1 in men's singles tennis by the Association of Tennis Professionals (ATP).

Novak Djokovic (Nole) was born on 22 May 1987 in Belgrade, SR Serbia, Yugoslavia, to parents Srđan and Dijana (née Žagar). He is of paternal Serbian and maternal Croatian descent. His two younger brothers, Marko and Djordje, have also played professional tennis.

Djokovic then competed at the Rogers Cup in Toronto, where he lost to Federer in the semi-finals. Djokovic also competed in doubles with Nadal in a one-time, high-profile partnership. This had not happened since 1976, when Jimmy Connors and Arthur Ashe as No. 1 and No. 2 paired together as a doubles team. They lost in the first round to Canadians Milos Raonic and Vasek Pospisil. Djokovic then lost to Roddick in the quarterfinals of the Cincinnati Masters.