Novak Djokovic’s quest for an unprecedented 25th Grand Slam title came to an abrupt and shocking halt at the 2024 US Open, where he was defeated in the opening round by Argentina’s Mariano Navone. The 39‑year‑old Serbian, who entered the tournament with hopes of adding a fifth US Open crown to his already impressive résumé, was forced to retire after a marathon five‑set match that lasted four hours and 36 minutes.

Navone, the world No. 49, secured a 7‑6 (7‑5), 5‑7, 4‑6, 6‑2, 6‑1 victory, marking one of the most surprising upsets in recent Grand Slam history.

The match was notable for several reasons. It became the longest first‑round encounter of Djokovic’s career at a major, and it represented his earliest departure from a Grand Slam tournament since the 2006 Australian Open.

Navone’s win also earned him the distinction of being the first player to defeat Djokovic in the opening round of the US Open, and the first to do so in the first round of any Grand Slam since Paul Goldstein’s upset at the 2006 Australian Open. Moreover, it was Navone’s inaugural triumph over a top‑10 opponent at a Grand Slam event.

From the outset, the conditions in New York proved unforgiving. The oppressive humidity and lingering heat took a severe toll on Djokovic’s body. Throughout the match, the Serbian champion experienced repeated bouts of nausea, vomiting, and debilitating cramping.

He later described his physical state as a “collapse” of his entire body, with his back and shoulder giving out during the later stages. These symptoms were not new for him; earlier in the season, Djokovic had disclosed that he suffers from a chronic health issue that flares up in hot and humid environments, a problem that has haunted him for years and has increasingly affected his performance. Despite the adversity, Djokovic fought valiantly. He took the first set in a tight tiebreak, leading 3‑0 before the set slipped away.

He managed to stay competitive in the second and third sets, but Navone’s relentless energy and precise shot‑making began to wear him down. By the fourth set, Djokovic’s condition had deteriorated further; he vomited again and struggled to maintain his footing on the court.

Navone, buoyed by his early success, broke Djokovic’s serve to take the set 6‑2, effectively sealing the match. The fifth set saw a visibly exhausted Djokovic attempting to rally, but his movement was hampered by cramping, and he committed an alarming 70 unforced errors.

He fought back tears on several occasions, acknowledging that he “despised every moment” he spent on the court. Navone, who idolized Djokovic as a child, expressed awe at sharing the stage with the greatest of all time, calling the experience "amazing" and saying he was "very happy" with his performance.

The aftermath of the match left many questions unanswered. Djokovic’s loss will likely see him drop out of the ATP top ten for the first time in eight years, a significant shift in the tennis hierarchy.

Fans and analysts are now speculating whether this could be his final appearance at a Grand Slam, given the severity of his health issues and the toll they have taken on his body. In addition to the men's singles upset, the tournament featured other notable moments. American Sofia Kenin overcame a second‑set challenge from fellow compatriot Venus Williams, clinching a 6‑2, 7‑6 (8‑6) victory in a match that began at 12:13 am, the latest start time for a women's match in US Open history. Williams, who has now suffered 14 consecutive singles defeats, continued a losing streak at the US Open that began in 2019.

Djokovic’s previous appearance at a tournament, two weeks earlier in Cincinnati, had already hinted at his physical struggles. He collapsed to his knees and vomited onto a towel after a loss to Thiago Tirante, later revealing that his chronic condition, exacerbated by heat and humidity, has been a persistent obstacle throughout the season. The US Open, broadcast live on Sky Sports and available for streaming without a contract on NOW, continues to deliver drama both on and off the court.

As the tournament progresses, the tennis world will watch closely to see how the remaining players adapt to the demanding New York conditions and whether Djokovic can recover in time for future events, such as the Laver Cup in London later this year. Overall, Navine’s victory over Djokovic will be remembered as a landmark upset, highlighting the unpredictable nature of Grand Slam tennis and underscoring the importance of physical resilience in the sport’s most demanding arenas.