Novak Djokovic’s quest for a record‑breaking 25th Grand Slam title was abruptly halted at the very first hurdle of the US Open, when Argentina’s Mariano Navone, ranked No. 49 in the world, delivered a stunning five‑set victory. The 39‑year‑old Serbian fell 7‑6 (7‑5), 5‑7, 4‑6, 6‑2, 6‑1 after a grueling 4‑hour‑36‑minute encounter that became the longest opening‑round match of Djokovic’s career and the earliest exit for a top player at a major since the 2006 Australian Open. Navone’s win marked several historic firsts: he became the inaugural player to defeat Djokovic in the first round of the US Open, the first to knock the Serbian out of a Grand Slam opening round since Paul Goldstein did so at the 2006 Australian Open, and he secured his maiden top‑10 scalp at a major tournament.

The Argentine, who captured his first ATP singles title earlier in the year, capitalised on the oppressive humidity that plagued the New York courts, while Djokovic struggled visibly with physical distress throughout the match. Statistically, Djokovic entered the contest with a 42‑12 record in five‑set battles, whereas Navone was 0‑4 in such matches.

Yet the Serbian’s usual resilience was undermined by severe cramping, pain, and repeated bouts of vomiting. He described the experience as "an awful feeling on the court," adding that his body seemed to "collapse" under the strain, with his back and shoulder giving out in the latter stages.

The lingering health issue he mentioned – a condition that has troubled him for years and flares up in heat and humidity – left him uncertain about his future in Grand Slam competition. The match’s drama unfolded in several stages. Djokovic surged ahead early, leading 3‑0 in the first set before a tie‑break saw the set slip away.

He managed to close the second set 6‑5 after a break, despite having vomited near the courtside towel box. The third set saw another bout of nausea, yet he still managed to capture a crucial break, moving one set away from victory. However, the fourth set began with another episode of vomiting, and Navone seized the momentum, breaking for 2‑1 and eventually taking the set 6‑2. In the decisive fifth set, Djokovic’s physical condition deteriorated further; he landed awkwardly after a mis‑hit, dropped his racket, and could barely move, allowing Navone to clinch the final set 6‑1.

Throughout the contest, Djokovic’s body language conveyed exhaustion and discomfort. He admitted to making 70 unforced errors and confessed that he "despised every moment" on the court. At one point he was on the verge of tears, and his performance was a stark contrast to the dominant displays that have defined his career.

The loss also guarantees his fall out of the ATP top ten for the first time in eight years, a significant shift in the sport’s hierarchy. Navone, who grew up idolising the Serbian champion, expressed both awe and gratitude after the win. "It was the best thing I've had on court," he said, marveling at the prestige of playing on such a grand stage and the opportunity to compete against the "GOAT". He praised the atmosphere and the challenge of a five‑set battle, acknowledging that the victory was a career‑defining moment.

The broader tournament narrative also featured other notable moments. American Sofia Kenin overcame a second‑set surge from fellow US player Venus Williams, winning 6‑2, 7‑6 (8‑6) in a match that began at 12:13 am – the latest start for a women's match in US Open history. Williams suffered her 14th consecutive singles defeat, extending a six‑match losing streak at the US Open that dates back to her 2019 victory. Djokovic’s health concerns had been hinted at earlier in Cincinnati, where he collapsed to his knees and vomited into a towel after a loss to Thiago Tirante.

He later disclosed that a long‑standing issue exacerbated by heat and humidity has been affecting him throughout the season. While New York’s conditions were milder than Cincinnati’s, the combination of high humidity and the intense pressure of a Grand Slam match proved too much on this occasion. The match also underscored a broader shift in men’s tennis: for the first time since 2003, none of the sport’s three most dominant figures – Djokovic, Roger Federer, or Rafael Nadal – progressed beyond the first round of a major tournament. This generational change opens the door for emerging talents like Navone to make deeper runs and reshape the competitive landscape.

As the US Open continues, Sky Sports will broadcast the remaining action, and fans can stream matches contract‑free via the NOW platform. Djokovic’s unexpected early exit leaves many questions about his future health and his ability to contend for further Grand Slam titles, while Navone’s breakthrough signals the rise of a new contender eager to challenge the established order.