Novak Djokovic

In 2001, Djokovic dominated the U14 circuit on the Tennis Europe Junior Tour, winning his first title in a second-category tournament in Messina, defeating compatriot Bojan Božović in the final, and his second in Livorno, where he beat top seed Andy Murray in the semifinals and second seed Aljoscha Thron in the final. In July, he won the U14 European Championship in Sanremo, defeating Lukáš Lacko in singles and the doubles with Božović against Russians Alexandre Krasnoroutskiy and Mikhail Bekker. He led Serbia to victory in the European Summer Cup, finishing the year as European champion in singles, doubles and team events. He also earned a silver medal at the ITF World Junior Championship U14 team competition for Yugoslavia. Djokovic ended 2001 ranked No. 1 on the ETA U14 list, with Murray in second place. In 2002, now competing in U16 events, Djokovic won two major tournaments in France: the Derby Cadets in La Baule, defeating Gaël Monfils in the final, and Le Pontet in Avignon. In September, he won his first ITF title in Pančevo, winning all matches in straight sets, including over No. 1 seed David Savić in the final. In November, Djokovic won the Prince Cup in Miami, defeating Stephen Bass in the final, shortly before competing at the Junior Orange Bowl, where he reached the third round before losing to Marcos Baghdatis. Overall, Djokovic compiled a 40–11 singles and 23–6 doubles record in juniors, achieving a combined junior world ranking of No. 24 in February 2004. His best junior Grand Slam result was reaching the semifinals of the 2004 Australian Open. He also competed at the 2003 French Open and 2003 US Open.

Djokovic played his first professional match in January 2003 at a Futures event in Oberschleißheim after receiving a wildcard from Niki Pilić, narrowly losing to Alex Rădulescu. He won his first Futures title in Belgrade later that year and ended 2003 ranked No. 687. In 2004, he recorded his first official ATP win during a Davis Cup match against Janis Skroderis, and later claimed his first Challenger title in Budapest on his 17th birthday. He made his ATP Tour main draw debut at the Croatia Open Umag and ended the year ranked No. 186. Djokovic's Grand Slam debut came at the 2005 Australian Open, followed by his first Slam win at the French Open. That year, he also reached the third round at both Wimbledon and the US Open, beating Gaël Monfils and Mario Ančić. He impressed at the Paris Masters by reaching the third round after defeating Mariano Puerta, ending the year ranked world No. 78 as the youngest player in the top 100.

On 9 April 2006, Djokovic secured a Davis Cup win for Serbia and Montenegro by defeating Greg Rusedski in four sets, giving his team a 3–1 lead over Great Britain and retaining their place in the Group One Euro/African Zone. Around this time, media reported his family had discussions with the Lawn Tennis Association about representing Great Britain. Djokovic, then world No. 64, initially dismissed the story, calling it a kind gesture following the tie. In 2009, he confirmed the talks were serious but chose to represent Serbia, saying he felt a strong national identity and wanted to remain true to it. Djokovic reached his first Grand Slam quarterfinal at the French Open as world No. 63, defeating ninth seed Fernando González en route. He retired against Rafael Nadal after two sets in their first career meeting, launching their historic rivalry. His performance pushed him into the top 40. At Wimbledon, he reached the fourth round before losing to Mario Ančić in five sets. Djokovic claimed his first ATP title at the Dutch Open in Amersfoort, defeating Nicolás Massú in the final without dropping a set. He won his second title at the Moselle Open in Metz, beating Jürgen Melzer, and broke into the top 20. He also made his first Masters quarterfinal at Madrid. He ended the season ranked No. 16, the youngest in the top 20.

Djokovic began 2007 by winning the Adelaide title, then reached the fourth round of the 2007 Australian Open, losing to eventual champion Roger Federer in straight sets. Strong showings at the Indian Wells and Miami Masters, where he finished runner-up and champion respectively, propelled him into the top 10. In Miami, he defeated Rafael Nadal in the quarterfinals and Guillermo Cañas in the final, earning his first Masters title and becoming the youngest champion there since Andre Agassi in 1990. He helped Serbia defeat Georgia in the Davis Cup, contributing a singles win. On clay, he won the Estoril Open against Richard Gasquet and reached the quarterfinals in Rome and Hamburg, losing to Nadal and Carlos Moyá respectively. At the French Open, he made his first major semifinal, falling to Nadal. At Wimbledon, Djokovic won a five-hour quarterfinal over Marcos Baghdatis before retiring in the semifinals against Nadal due to elbow issues.

Djokovic’s breakthrough continued at the Canadian Open, where he defeated world No. 3 Andy Roddick, No. 2 Nadal, and No. 1 Federer to claim the title. He became the first player since Boris Becker in 1994 to beat the top three ranked players in a single event, and only the second after Tomáš Berdych to defeat Federer and Nadal as world No. 1 and 2. Björn Borg remarked Djokovic was “definitely a contender to win a Grand Slam”. Djokovic would then go on to reach his first major final at 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 the year at the Hopman Cup alongside fellow Serbian Jelena Janković. He won all four of his singles matches, including a final win over Mardy Fish, but Serbia lost the decisive mixed doubles rubber against the United States. The event also marked his first competitive match against Serena Williams. At the Australian Open, Djokovic reached the final without dropping a set, defeating two-time defending champion Roger Federer in the semifinals. By reaching the semis, he became the youngest Open Era player to make the last four at all four majors. He beat unseeded Jo-Wilfried Tsonga in four sets in the final, claiming his first Grand Slam singles title. It was the first major title since the 2005 Australian Open not won by Roger Federer or Rafael Nadal.

Djokovic then reached the semifinals in Dubai, and won titles at Indian Wells and the Italian Open, his third and fourth Masters titles respectively. He lost to Nadal in the semifinals of both Hamburg and the 2008 French Open. On grass, he fell to Nadal in the Queen’s Club final and suffered a second-round loss at Wimbledon to Marat Safin, ending a streak of five straight major semifinals. He was a quarterfinalist at the Rogers Cup and a finalist in Cincinnati, ending Nadal's 32-match win streak in the semis. In the final, he again lost to Andy Murray. At the 2008 Summer Olympics, he earned a bronze medal in the singles event and exited in the first round in doubles with partner Nenad Zimonjić.

In November, Djokovic won his first year-end championship title at the Tennis Masters Cup in Shanghai, beating Nikolay Davydenko in the final.

Djokovic began the year at the Brisbane International, where he was upset in the first round by fellow Pilić academy trainee Ernests Gulbis. At the Australian Open, he retired in the quarterfinals against Andy Roddick due to heat-related illness. After a semifinal loss to Jo-Wilfried Tsonga in Marseille, Djokovic won the Dubai Championships, defeating David Ferrer for his 12th career title. At the Indian Wells Masters, he lost to Roddick in the quarterfinals. He then reached the final of the Miami Open, defeating Roger Federer in the semifinals before losing to Andy Murray. During the clay season, Djokovic reached finals at both the Monte Carlo Masters and Italian Open, losing to Rafael Nadal each time. He then claimed his second title of the year at the inaugural Serbia Open, defeating Łukasz Kubot in the final. At the Madrid Open, he lost another close semifinal to Nadal in a record-setting match lasting 4 hours and 3 minutes. He exited the French Open in the third round to Philipp Kohlschreiber. Djokovic reached the final of the Gerry Weber Open on grass, losing to Tommy Haas, and then fell to Haas again in the quarterfinals of Wimbledon. During the 2009 US Open Series, he reached the quarterfinals in Montreal, then made the final in Cincinnati, beating Nadal in the semifinals before falling to Federer. At the US Open, he reached the semifinals, where he was again defeated by Federer.

After playing nearly 100 matches in 2009, Djokovic opted to skip early ATP tournaments in 2010 and began the season at the exhibition AAMI Classic, defeating Tommy Haas but losing to Fernando Verdasco and Bernard Tomic. At the Australian Open, he fell to Jo-Wilfried Tsonga in the quarterfinals despite being a set away from victory. He then reached the semifinals in Rotterdam and won the Dubai Championships, defending an ATP title for the first time. In March, he led Serbia to a 3–2 win over the United States in the 2010 Davis Cup, defeating Sam Querrey and John Isner. After early losses in Indian Wells and Miami, he split with coach Todd Martin. He reached the semifinals of the Monte Carlo Masters and the quarterfinals in Rome, both times losing to Verdasco. At the 2010 Serbia Open, he withdrew while trailing Filip Krajinović, marking his only loss to a player ranked outside the Top 200. At the French Open, he lost to Jürgen Melzer in the quarterfinals after leading by two sets — the only time in his career he lost a major match from that position. He captured his first ATP doubles title at the Aegon Championships with Jonathan Erlich. At Wimbledon, he lost in the semifinals to Tomáš Berdych. At the Canadian Open, Djokovic reached the semifinals, losing to Federer. He also teamed with Nadal in doubles, marking the first pairing of world No. 1 and No. 2 players since Jimmy Connors and Arthur Ashe in 1976.

Djokovic opened the season by winning the Australian Open, dropping just one set and defeating Roger Federer in the semifinals and Andy Murray in the final to claim his second title in Melbourne. He continued his run by beating Federer in the final of the Dubai Championships. At Indian Wells and Miami, he defeated both Federer and Rafael Nadal to claim back-to-back Masters 1000 titles—becoming only the third player to beat both in the same event twice. After winning the Serbia Open, he extended his unbeaten streak with titles in Madrid and the Italian Open, defeating Nadal in straight sets in both finals—his first wins over Nadal on clay after nine straight losses. At the French Open, Djokovic reached the semifinals before falling to Federer in four sets—his first loss of the year, snapping a 43-match win streak and ending a perfect 41–0 start to the season. Five weeks later, Djokovic claimed his first Wimbledon title, defeating Nadal in the final, and secured the world No. 1 ranking for the first time in his career.

Djokovic began the season by winning the Australian Open, defeating David Ferrer in the quarterfinals, and Andy Murray in a five-set semifinal lasting 4 hours and 50 minutes. In the final, he beat Rafael Nadal in five sets. At 5 hours and 53 minutes, it was the longest Grand Slam final and longest match in Australian Open history. He lost to John Isner in the semifinals of Indian Wells but retained his Miami title by defeating Murray. Djokovic fell to Nadal in the finals of both Monte Carlo and the Italian Open. At the French Open, he reached his first final at the tournament, defeating Roger Federer in the semis. Attempting to hold all four majors at once, he lost to Nadal in four sets. At Wimbledon, he was again beaten by Federer in the semifinals. Djokovic was Serbia's flag bearer at the 2012 Summer Olympics in London. He beat Jo-Wilfried Tsonga to reach the semifinals but lost to Murray and then to Juan Martín del Potro in the bronze medal match, finishing fourth. He defended his Rogers Cup title, dropping just one set, but lost the Cincinnati Masters final to Federer.

Djokovic began his 2013 season at the 2013 Hopman Cup, representing Serbia with Ana Ivanovic. He won three of his four singles matches, including a final-round win over Fernando Verdasco, but Serbia lost the final 1–2 to Spain. At the Australian Open, he defeated Stan Wawrinka in a memorable fourth-round match lasting over five hours, and went on to beat Andy Murray in the final to win a record third consecutive Australian Open title in the Open Era. Djokovic next helped Serbia take a 2–0 lead over Belgium in the 2013 Davis Cup World Group first round, with a straight-sets win over Olivier Rochus. He then won the 2013 Dubai Tennis Championships, defeating Tomáš Berdych in the final. At Indian Wells, Djokovic's 22-match winning streak was ended by Juan Martín del Potro in the semifinals. At the Miami Masters, he was upset in the fourth round by Tommy Haas. In Davis Cup quarterfinals, Djokovic helped Serbia defeat the United States with wins over John Isner and Sam Querrey. He then won the 2013 Monte-Carlo Rolex Masters, defeating Rafael Nadal in straight sets to end Nadal’s 46-match winning streak at the event. He suffered early exits at the Madrid Open and Rome Masters, losing to Grigor Dimitrov and Berdych, respectively. At the 2013 French Open, Djokovic advanced to the semifinals, defeating Wawrinka, Dimitrov, Philipp Kohlschreiber, and Tommy Haas, before losing a dramatic five-set match to Nadal. At Wimbledon, Djokovic defeated Del Potro in a historic semifinal lasting 4 hours and 44 minutes, but lost the final to Murray in straight sets. Djokovic was a finalist at the US Open, where he lost to Nadal in four sets. He later won the China Open and the Shanghai Masters, extending his unbeaten streak in Asia to 20 matches. He then claimed the Paris Masters, defeating David Ferrer in the final. Djokovic ended the year by winning the 2013 ATP World Tour Finals, beating Nadal in the final. He concluded the season with a 24-match winning streak and later announced that Boris Becker would join his team as head coach for 2014.

Djokovic began the year by winning the Mubadala World Tennis Championship. At the Australian Open, he reached the quarterfinals with four straight-set wins before losing to Stanislas Wawrinka in five sets, ending his 25-match win streak in Melbourne and 14 consecutive Grand Slam semifinals. He won the Indian Wells Masters, defeating Roger Federer, and the Miami Masters by beating Rafael Nadal. A wrist injury affected his Monte Carlo campaign, where he lost to Federer in the semifinals. After recovery, he won the Italian Open over Nadal and donated his $500,000 prize to victims of the 2014 Southeast Europe floods. At the French Open, Djokovic dropped only two sets en route to the final but lost to Nadal in four sets, his first loss to him after four wins. Djokovic won his second Wimbledon title by defeating Federer in five sets in the final, reclaiming the world No. 1 ranking. He suffered early exits at the Canadian Open (to Jo-Wilfried Tsonga) and Cincinnati (to Tommy Robredo). At the US Open, he reached the semifinals but lost to Kei Nishikori. He won a fifth China Open title in six years, and after a semifinal loss to Federer in Shanghai, claimed the Paris Masters without dropping a set. At the ATP Finals, he set a record by dropping just nine games in the round-robin stage. By reaching the semifinals, Djokovic secured the year-end No. 1 ranking for the third time, tying Nadal for fifth most.

Djokovic started 2015 at the Qatar Open in Doha, winning his first two rounds easily but losing in the quarterfinals to Ivo Karlović. He bounced back at the Australian Open, reaching the final without dropping a set until a tough semifinal against defending champion Stan Wawrinka. Djokovic won the final against Andy Murray in four sets, earning a record fifth Australian Open title and moving into equal eighth on the all-time Major titles list. He then finished runner-up to Roger Federer at the Dubai Championships. Shortly after, Djokovic won his 21st Masters title at Indian Wells, defeating Federer in the final. He followed this with a fifth title at Miami, beating Andy Murray, and became the first player to win the Indian Wells–Miami double three times. In April, Djokovic won the Monte-Carlo Masters for the second time, becoming the first man to win the first three Masters 1000 events of the season. He withdrew from the 2015 Madrid Masters but then captured the Rome Masters, making it 4 Masters titles out of 4 entered that season. At the French Open, Djokovic reached the final without dropping a set in the first five rounds, including a win over Rafael Nadal and a marathon semifinal against Andy Murray. However, he lost the final to Stan Wawrinka. Five weeks later, Djokovic came back from two sets down to beat Kevin Anderson and won his third Wimbledon title, defeating Federer in four sets. Djokovic had the chance to complete the Career Golden Masters at the Cincinnati Masters but lost the final to Federer. He would complete the feat in later years. At the US Open, Djokovic reached his sixth final, beating Federer in four sets to win his third Grand Slam of the year and tenth overall, becoming only the fifth man in the Open Era with double-digit Grand Slam titles. He ended the season by winning the China Open for a sixth time, defeating Nadal in the final to improve his unbeaten record at the tournament to 29–0.

Djokovic won his 60th career title in Doha, defeating Rafael Nadal in 73 minutes. He broke his ATP ranking points record, reaching 16,790. Djokovic then claimed his sixth Australian Open, beating Roger Federer in the semifinals and Andy Murray in the final. After recovering from an eye infection at the Dubai Championships, he won his fifth Indian Wells Masters title, beating Nadal and Milos Raonic. Djokovic’s dominance meant world Nos. 2 and 3 combined points still wouldn’t surpass him. On 3 April 2016, Djokovic won the Miami Open without dropping a set, claiming his sixth title and tying Andre Agassi's record. This was his fourth Sunshine Double, most in history, and third consecutive. The win made him the all-time ATP prize money leader with $98.2 million. After an early exit at the Monte-Carlo Masters, Djokovic won the Madrid Open beating Murray in the final. The next week at the Rome Masters, Murray defeated Djokovic; Djokovic still beat Nadal and Kei Nishikori in earlier rounds. Djokovic won the French Open, defeating Murray in four sets, completing the historic Nole Slam. This made Djokovic the eighth player to achieve a Career Grand Slam, third after Don Budge and Rod Laver to hold all four major titles simultaneously, and the first to earn $100 million in prize money. His ranking points rose to a record 16,950. At Wimbledon, Djokovic's 30-match Grand Slam winning streak ended with a third-round loss to Sam Querrey, his earliest Slam exit since the 2009 French Open. In late July, Djokovic returned to form, winning his fourth Canadian Open title, his 30th Masters overall...

In January, Djokovic defended his title in Doha, defeating world No. 1 Andy Murray. At the Australian Open, he lost in the second round to No. 117 Denis Istomin, marking his first early exit since 2007 and first loss at a major to a player outside the top 100. In February and March, he was eliminated before semifinals by Nick Kyrgios at the Mexican Open and Indian Wells Masters. In April, Djokovic reached the quarterfinals of the Monte-Carlo Masters, losing to David Goffin. He then split with longtime coach Marián Vajda, fitness coach Gebhard Phil-Gritsch, and physiotherapist Miljan Amanović to find a new spark. He reached the semifinals at the Madrid Masters, losing to Rafael Nadal, and was runner-up at the Rome Masters. On 21 May, Djokovic announced Andre Agassi as his new coach starting at the French Open, where he lost in the quarterfinals to Dominic Thiem. He began the grass season at the Eastbourne International, winning the title by beating Gaël Monfils—his only tournament win without Vajda until their 2022 split. At Wimbledon, he retired in the quarterfinals against Tomáš Berdych due to an elbow injury. On 26 July, Djokovic announced he would miss the US Open and the rest of the season to recover from his injury. This ended his streak of 51 consecutive Grand Slam appearances since his debut in 2005.

In January, Djokovic won the Kooyong Classic exhibition against Dominic Thiem. At the 2018 Australian Open, he reached the fourth round before losing to Chung Hyeon. In late January, he underwent elbow surgery. He returned to practice by early March, and played at Indian Wells a week later, losing in the second round to Taro Daniel. He also lost early at the Miami Open to Benoît Paire. Reuniting with coach Marián Vajda at the Monte-Carlo Masters, Djokovic defeated Dušan Lajović and Borna Ćorić, before losing to Dominic Thiem. He said, "After two years finally I can play without pain." Following an early loss at Barcelona to Martin Kližan, he showed improvement at the Madrid Masters by beating Kei Nishikori—his first top 20 win in 10 months—but lost to Kyle Edmund in the second round.

Djokovic began 2019 at the Qatar Open, losing in the semifinals to Roberto Bautista Agut. As top seed at the Australian Open, he defeated Rafael Nadal in the final to claim his record seventh Australian Open and 15th major title. He was then upset by Philipp Kohlschreiber at the Indian Wells Masters third round, and lost in the fourth round of the Miami Open to Bautista Agut. On clay, Djokovic reached the quarterfinals of the Monte-Carlo Masters, losing to Daniil Medvedev. During the Madrid Open, he celebrated his 250th week at world number 1 in the ATP rankings and won the title by defeating Stefanos Tsitsipas. At the Italian Open, he reached the final after beating Juan Martín del Potro, but lost to Nadal. At the French Open, Djokovic reached the semifinals without dropping a set, becoming the first man to reach 10 consecutive French Open quarterfinals. He lost a marathon five-set match to Dominic Thiem, ending a 26-match winning streak in majors and his bid for a second 'Nole Slam'. Djokovic defended his title at Wimbledon, beating Roger Federer in a record 4-hour 57-minute five-set final. Despite winning fewer points, Djokovic saved two championship points to claim his fifth Wimbledon and 16th major title. He lost in the semifinals of the Cincinnati Open to eventual champion Medvedev, and retired injured in the fourth round of the US Open against Stan Wawrinka. In October, Djokovic won the Japan Open over John Millman but lost in the quarterfinals of the Shanghai Masters to Tsitsipas. He ended the season by winning his fifth Paris Masters title against Denis Shapovalov.

At the inaugural 2020 ATP Cup, Djokovic led Serbia to victory with six wins, including over Daniil Medvedev in the semifinals and Rafael Nadal in the final. At the Australian Open, he beat Roger Federer in the semifinals and defeated Dominic Thiem in five sets in the final, earning his eighth Australian Open and 17th Grand Slam title. He regained the world No. 1 ranking and became the first player in the Open Era to win Grand Slams in three different decades. It was also his first comeback win from two sets to one down in a major final. Djokovic then claimed his fifth title at the Dubai Championships, defeating Stefanos Tsitsipas in the final. In June, during the Adria Tour he organized, Djokovic tested positive for COVID-19, along with several other participants, prompting criticism over the event's lack of safety protocols. Djokovic later apologized, saying they believed the tournament met all health guidelines, but acknowledged they "were wrong". He later described the criticism as part of a "witch hunt".

Djokovic began the year at the 2021 ATP Cup, winning both singles matches, but Serbia exited in the group stage. He then won his ninth Australian Open title and 18th major overall, defeating Daniil Medvedev in the final. On 1 March, Djokovic tied and then surpassed Roger Federer's Open Era record of 310 weeks as world No. 1. He suffered early losses at the Monte-Carlo Masters (to Dan Evans) and Serbia Open (to Aslan Karatsev), and reached the final of the Italian Open, defeating Stefanos Tsitsipas and Lorenzo Sonego, before losing to Rafael Nadal.

At the French Open, he beat Nadal in a four-set semifinal and came from two sets down to defeat Tsitsipas in the final. He became the first man in the Open Era to win a major after coming from two sets down twice in the same event, and the first to win all four majors at least twice in the Open Era. At Wimbledon, he earned his 100th grass-court win en route to the final, where he defeated Matteo Berrettini to win his sixth title and 20th major, tying Federer and Nadal. He became the second man to win majors on all three surfaces in a single year (a "Surface Slam"), and the fifth in the Open Era to achieve the Channel Slam (French Open and Wimbledon in the same year). At the 2020 Summer Olympics, Djokovic sought a gold medal, but lost to Alexander Zverev in the semifinals and to Pablo Carreño Busta in the bronze match. In mixed doubles, partnering Nina Stojanović, they reached the semifinals but withdrew from the bronze medal match due to Djokovic's shoulder injury.

Djokovic was set to start his 2022 season at the ATP Cup in Sydney but withdrew. To compete in the Australian Open, players were required to be vaccinated against COVID-19 or have a medical exemption. Djokovic received an exemption from Tennis Australia and the Department of Health (Victoria), citing a positive COVID-19 test on 16 December 2021. He was granted a visa on 18 November 2021 and arrived in Melbourne on 5 January, but was detained by the Australian Border Force for failing to meet entry requirements for unvaccinated travellers. Djokovic later admitted an error in his travel declaration form, as he had been in Spain shortly before arriving. His visa was cancelled, and he was held in a detention hotel pending appeal. On 10 January, the Federal Circuit and Family Court of Australia ruled in Djokovic’s favour, ordering his release and noting that he was denied enough time to consult with lawyers and tennis officials before his interview. However, on 14 January, Alex Hawke, the Minister for Immigration, Citizenship, Migrant Services and Multicultural Affairs, cancelled Djokovic’s visa again under the Migration Act 1958, citing public health and order concerns. The Federal Court of Australia upheld the decision, and Djokovic was deported on 16 January.

In February, Djokovic returned at the Dubai Championships, where vaccination was not required. He lost in the quarterfinals to Jiří Veselý, resulting in the loss of his world No. 1 ranking to Daniil Medvedev. It was the first time since 2004 that a player outside the Big Four held the top spot. Djokovic withdrew from the Indian Wells Masters and Miami Open due to U.S. entry restrictions on unvaccinated foreigners. Despite not playing, he regained No. 1 when Medvedev lost early at Indian Wells. He began his clay season at the Monte-Carlo Masters, losing his opening match to Davidovich Fokina. At the Serbia Open, he reached the final but lost to Andrey Rublev. In May, he was beaten by Carlos Alcaraz in the Madrid Open semifinals. A week later, he won the Italian Open, his sixth title there and a record-extending 38th Masters crown, after defeating Stefanos Tsitsipas in the final. In the semis, he claimed his 1,000th career win by beating Casper Ruud. At the French Open, he advanced to the quarterfinals without dropping a set, but lost to Rafael Nadal in their record 59th match, ending his title defense and again dropping to No. 2. At Wimbledon, he earned his 80th win at each major with a first-round victory over Kwon Soon-woo, becoming the first player to do so. He reached a record 32nd Grand Slam final after defeating Cameron Norrie in the semifinals and beat Nick Kyrgios in four sets to claim his seventh Wimbledon and 21st major title, surpassing Roger Federer and moving one behind Nadal. Due to U.S. travel restrictions for unvaccinated foreigners, Djokovic was unable to enter the country and withdrew from the US Open.

Djokovic opened the year with his 92nd title at the Adelaide International, saving a championship point to beat Sebastian Korda. At the Australian Open, despite a hamstring issue, he defeated Stefanos Tsitsipas in the final to claim a record-extending 10th title, tie Rafael Nadal's men's record of 22 majors, and reclaim the No. 1 ranking. On 27 February, Djokovic surpassed Steffi Graf with his 378th week at No. 1, setting a record across both tours. He missed the Indian Wells and 2023 Miami Open due to U.S. entry restrictions. During the clay season, he exited early at the Monte-Carlo Masters and Banja Luka Open, and lost in the Rome quarterfinals. At the French Open, Djokovic defeated world No. 1 Carlos Alcaraz in the semis and beat Casper Ruud in the final to win a record-breaking 23rd major, becoming the first man to achieve a triple Career Grand Slam. He also regained the top ranking. At Wimbledon, Djokovic reached his 9th final after wins over Pedro Cachin, Thompson, Stan Wawrinka, Hubert Hurkacz, Andrey Rublev, and Jannik Sinner. He lost the final to Alcaraz in five sets, ending a 34-match winning streak at Wimbledon. Djokovic then won the Cincinnati Masters, beating Alcaraz in 3 hours and 49 minutes in the longest best-of-three-set ATP final, hailed as one of the greatest matches ever.

At the Australian Open, Djokovic reached the semifinals but lost to world No. 4 Jannik Sinner in four sets, ending his 33-match win streak at the event and marking his first semifinal defeat there. He called it "one of the worst Grand Slam matches I've ever played". Nonetheless, he equaled Roger Federer's record of 58 Grand Slam singles quarterfinals and retained his world No. 1 ranking. Djokovic returned to the Indian Wells Masters for the first time since 2019, but lost in the third round to Luca Nardi, ranked No. 123—the lowest-ranked player to beat him at a Masters 1000 or Grand Slam. At the 2024 Monte-Carlo Masters, he reached the semifinals but lost to Casper Ruud. In Rome, after being accidentally struck by a water bottle post-match, he lost in the third round to Alejandro Tabilo. At the 2024 Geneva Open, he earned his 1,100th career win on his 37th birthday, becoming the third man in the Open Era to reach that mark, and holding the highest win percentage among them (83.5%). At the French Open, Djokovic survived a five-set match against Lorenzo Musetti that ended at 3:07 a.m.—the latest finish in tournament history. In the fourth round, he defeated Francisco Cerúndolo in his longest French Open match (4h39m), surpassing Federer's records for most Grand Slam match wins and quarterfinal appearances. However, he suffered a torn medial meniscus in his right knee during that match and withdrew before the quarterfinals, losing the No. 1 ranking to Sinner. At the Wimbledon Championships, Djokovic reached his 37th Grand Slam final, aiming to equal Federer’s record of eight titles, but lost in straight sets to Carlos Alcaraz in a repeat of the 2023 final. At the 2024 Summer Olympics, Djokovic defeated Matthew Ebden, Rafael Nadal, Dominik Koepfer, Stefanos Tsitsipas, and Lorenzo Musetti to reach his first Olympic final. He then beat Carlos Alcaraz in straight sets to win the gold medal, completing a Career Golden Slam and Career Super Slam.

Djokovic opened the 2025 season at the Brisbane International, losing to Reilly Opelka in the quarterfinals. His second round match at the Australian Open marked his 430th career major main draw singles match, surpassing Roger Federer's all-time record. After defeating Jiri Lehecka in the fourth round, he prevailed over Carlos Alcaraz once again in four sets. However, Djokovic's run ended when he retired in his semifinal match against Alexander Zverev due to a muscle tear after only one set played.

Djokovic then participated in the newly upgraded ATP 500 Tournament in Doha, but lost to Matteo Berrettini in the first round. This marked the first time Djokovic lost in any first round since the 2016 Summer Olympics.

Djokovic's next tournament was the Indian Wells Open, where he suffered a 2nd round defeat to lucky loser Botic van de Zandschulp – the 2nd year in a row where he lost to a lucky loser at the same tournament, following Luca Nardi.

At the 2025 Miami Open, Djokovic reached the third round defeating Rinky Hijikata and equalled Rafael Nadal’s record number of Masters 1000-level wins at 410. With his win over lucky loser Camilo Ugo Carabelli in the third round, Djokovic claimed his 411th career main draw win at Masters 1000 level, surpassing Nadal's record.

In May 2025, it was announced that Andy Murray would no longer be working as Djokovic's coach, by mutual agreement reached after Djokovic started working with Murray in November 2024. Djokovic took a last minute entry to the 2025 Geneva Open, where he defeated Hubert Hurkacz in the final to claim the 100th ATP singles title of his career, becoming the first ever tennis player to win at least one ATP singles title in twenty consecutive seasons. At the French Open, Djokovic reached a record-extending 51st major semifinal, where he lost in straight sets to world no. 1 Jannik Sinner. By winning the quarterfinals, he recorded his 101st wins at the tournament, the second most after Rafael Nadal.