Novak Djokovic’s quest for a record‑breaking 25th Grand Slam title came to an abrupt and unexpected halt at the 2026 US Open, where he was defeated by Argentina’s Mariano Navone in a grueling five‑set encounter. The 39‑year‑old Serbian, who entered the tournament hoping to add another major to his illustrious résumé, was forced to retire after a match that lasted four hours and 36 minutes, succumbing 7‑6 (7‑5), 5‑7, 4‑6, 6‑2, 6‑1.

This loss not only marked the longest opening‑round match of Djokovic’s Grand Slam career but also represented his earliest departure from a major since the 2006 Australian Open, where Paul Goldstein became the last player to eliminate him in a first‑round match. Navone, ranked world No. 49, achieved a historic victory by becoming the first player to beat Djokovic in a US Open first round and the first to do so in any Grand Slam first round in two decades.

The Argentine also recorded his first top‑10 win at a major tournament, a milestone that will likely boost his confidence and visibility on the tour. The match unfolded under oppressive humidity, a condition that seemed to exacerbate Djokovic’s physical struggles. Throughout the contest, the Serbian champion appeared to be battling more than just his opponent; he was visibly hampered by cramping, severe fatigue, and repeated bouts of vomiting.

At several points he was forced to pause, leaning on the court’s edge and wiping sweat from his brow, while his body seemed to “collapse” under the strain, as he later described. Statistically, Djokovic entered the match with a 42‑12 record in five‑set battles, whereas Navone had never won a five‑setter before (0‑4). Nevertheless, the Argentine’s relentless baseline play and his ability to stay composed in the humid conditions allowed him to outlast the Serbian legend. Djokovic’s performance was marred by physical distress: he vomited multiple times, his back gave out, and his shoulder felt unreliable, making it impossible to finish the match in his usual dominant fashion.

After the loss, he admitted that the experience was far from enjoyable, saying, “I didn’t enjoy myself. It was an awful feeling on the court for me.” He added that the health issue he has been coping with for years—exacerbated by heat and humidity—had finally taken its toll.

The defeat raises unsettling questions about Djokovic’s future at the sport’s biggest stages. Could this be his final appearance at a Grand Slam, or at least the last one where he competes at his historically high level? The Serbian’s recent health concerns were hinted at during his Cincinnati outing two weeks earlier, where he collapsed to his knees and was seen vomiting into a towel after a loss to Thiago Tirante. He later disclosed that a chronic condition, aggravated by hot and humid environments, has plagued him throughout the season.

While the New York heat was not as extreme as Cincinnati’s, Djokovic’s cheeks were already flushed and his hair drenched in sweat early in the first set, which he initially led 3‑0 before losing it in a tiebreak. In an effort to mitigate the conditions, Djokovic successfully requested the roof to be closed over Arthur Ashe Stadium.

Even with the roof and the air‑conditioning turned on, his body continued to rebel. He managed to break Navone’s serve late in the second set after a bout of vomiting near the courtside towel box, pulling the set to 6‑5 before serving it out. The third set saw another episode of nausea, yet he still captured a crucial break, moving one set away from victory.

However, the fourth set began with another vomiting spell, and despite breaking once more for a 2‑1 lead, Navone’s resilience proved decisive. A mis‑step after a wide shot in the fourth set saw Djokovic land awkwardly, drop his racket, and effectively concede the set. The match concluded just before midnight, with Navone securing the final set 6‑1.

It marked the first time since 2003 that none of the sport’s modern “Big Three” – Djokovic, Roger Federer, or Rafael Nadal – advanced beyond the second round of a Grand Slam. Throughout the fifth set, Djokovic appeared to be cramping, moving sluggishly, and fighting through pain, ultimately committing 70 unforced errors.

He fought back tears during the final games, acknowledging that he “despised every moment” he spent on the court. Navone, who idolized Djokovic growing up, expressed awe at having shared the court with the GOAT. “It was the best thing I’ve had on court.

This is an amazing stadium and the biggest stage. Playing five sets against him is a dream.

I’m very happy,” he said, reflecting on the significance of the victory for his career. As a result of the loss, Djokovic is set to fall out of the ATP top 10 for the first time in eight years, a stark reminder of how physical health can influence even the most dominant athletes.

The broader tennis community will watch closely to see how the Serbian legend manages his condition moving forward, whether he can adapt his schedule, or if he might need to reconsider his participation in future majors. Meanwhile, the US Open continued with other notable matches.

American Sofia Kenin held off a late surge from fellow countrywoman Venus Williams, clinching a 6‑2, 7‑6 (8‑6) victory that featured a historic late‑night start at Arthur Ashe Stadium, the latest women's match kickoff in tournament history. Williams suffered her 14th consecutive singles defeat, extending a losing streak that began after her last win in Washington in July 2025.

The tournament’s coverage remains accessible via Sky Sports, NOW, and the Sky Sports app, offering live scores, video highlights, and in‑depth analysis for fans worldwide. As the US Open progresses, the tennis world will reflect on Djokovic’s unexpected exit, Navone’s breakthrough, and the ever‑evolving narratives that make Grand Slam events compelling spectacles.