Novak Djokovic’s quest for an unprecedented 25th Grand Slam title ended in dramatic fashion on the opening night of the US Open, as the 39‑year‑old Serbian was defeated by Argentina’s rising star Mariano Navone in a grueling five‑set battle that stretched to four hours and 36 minutes. The match, which concluded just before midnight, saw the world No. 49 overturn a 7‑6 (7‑5), 5‑7, 4‑6, 6‑2, 6‑1 scoreline, delivering one of the most surprising first‑round upsets in recent tennis history.

Navone’s victory marked several notable firsts. He became the inaugural player to eliminate Djokovic in the opening round of a US Open, and the first to do so at any Grand Slam since Paul Goldstein’s upset of the Serbian at the 2006 Australian Open.

Additionally, Navone secured his maiden top‑10 win on the sport’s biggest stages, a milestone that will likely accelerate his ascent in the ATP rankings. The match itself was a test of endurance and resilience.

Djokovic entered the contest with a 42‑12 record in five‑set encounters, while Navone had yet to win a five‑setter at the tour level, standing at 0‑4. Despite the disparity, the Argentine displayed remarkable composure, gradually eroding the Serbian’s early advantage. The first set was tightly contested, with Djokovic edging it in a tiebreak after a 3‑0 lead that slipped away. However, the humid conditions inside Arthur Ashe Stadium began to take a toll on the Serbian champion.

Throughout the night, Djokovic struggled with severe physical distress. He repeatedly vomited, a symptom he later attributed to a long‑standing health issue that is exacerbated by heat and humidity.

"I’ve been dealing with this for years," Djokovic explained after the match, "and today my body just collapsed – cramping, pain, my back gave out, my shoulder gave out, and I couldn’t finish the match. I don’t know if it can be fixed.

I’m trying, I’m trying." The Serbian’s discomfort was evident from the start. By the midpoint of the first set, his cheeks were flushed and sweat drenched his hair, despite the roof being closed to mitigate the heat.

After a brief pause, he managed to secure a crucial break at 6‑5 in the second set, only to vomit again near the courtside towel box. The pattern repeated in the third and fourth sets, with each episode sapping his energy and limiting his movement. By the time the fifth set began, Djokovic was visibly weakened, his steps sluggish, and his strokes lacking their usual precision.

Navone, a 25‑year‑old who captured his first ATP singles title earlier in the year, never relented. He capitalized on Djokovic’s faltering footwork, breaking serve at pivotal moments and maintaining relentless pressure.

In the fourth set, after Djokovic’s fourth‑set break, the Argentine surged ahead, ultimately sealing the set 6‑2. The final set saw Navone dominate, winning 6‑1 as Djokovic’s body continued to protest. The emotional weight of the loss was palpable.

Djokovic, known for his stoic demeanor, admitted he "despised every moment" on the court and that the experience was "not enjoyable" at all. He fought back tears in the fifth set, a rare display of vulnerability for the multiple‑Grand Slam champion.

His unforced error count ballooned to 70, underscoring how far his physical condition had deteriorated. Beyond the immediate shock, the result carries broader implications for the sport.

Djokovic’s early exit represents the first time since 2003 that none of the so‑called "Big Three" – Djokovic, Roger Federer, or Rafael Nadal – advanced beyond the first round of a major tournament. It also signals a potential shift in the ATP rankings; with this defeat, Djokovic is poised to drop out of the top ten for the first time in eight years, ending a remarkable run of consistency. Navone’s post‑match comments reflected both awe and humility. "Playing against the GOAT on this court is an incredible feeling," he said, describing the atmosphere as "amazing" and expressing gratitude for the opportunity to compete on such a grand stage.

His admiration for Djokovic was evident, noting that the Serbian had been a childhood idol. The match also highlighted the ongoing challenges that elite athletes face when competing in humid, indoor environments. While the US Open has the capability to close its roof, the combination of high humidity and temperature can still create taxing conditions, especially for players with pre‑existing health concerns.

Djokovic’s struggle underscores the importance of medical monitoring and adaptive strategies for longevity in the sport. In addition to the men’s singles upset, the evening featured a notable women’s match where American Sofia Kenin edged Venus Williams 6‑2, 7‑6 (8‑6) after a hard‑fought second‑set tiebreak. The contest began at 12:13 am, marking the latest start time for a women’s match in US Open history. Williams suffered her 14th consecutive singles loss, a streak that began after her last victory in Washington in July 2025, and has now lost six straight matches at the US Open since her 2019 triumph.

Overall, the night was a reminder that even the most dominant champions are vulnerable to the unpredictable variables of health, environment, and emerging talent. As the tournament progresses, fans will watch closely to see whether Djokovic can recover for future Grand Slams or if this signals the twilight of his era.

Meanwhile, Navone’s breakthrough performance will likely inspire other up‑and‑coming players to believe that with perseverance, they too can topple the giants of the game.