For nearly two decades, Novak Djokovic has owned a perfect record at the opening round of the US Open. That unbroken streak came to a stunning and emotional end on the opening days of the 2026 tournament, where 39-year-old tennis legend dropped a five-set defeat to Argentina’s 25-year-old Mariano Navone, capping a match marked by visible physical struggle and uncharacteristic vulnerability.
Djokovic, a 24-time Grand Slam champion and the tournament’s fourth seed, entered the match having never fallen in the opening round at Flushing Meadows, and had not lost a first-round Grand Slam match since 2002. Through the four-hour contest in New York’s oppressive humidity, the Serbian icon fought through severe physical distress, repeatedly feeling nauseous and vomiting into a court-side towel bin, before ultimately succumbing to a 7-6 (7-5), 5-7, 4-6, 6-2, 6-1 defeat.
The match unfolded with a promising start for Djokovic, who broke Navone’s first serve and jumped to an early 4-1 lead. But a grueling extended rally sapped his energy, and his physical struggles quickly derailed his momentum. By the end of the first set, he was bent over double between points, his serve and groundstroke speed dropped dramatically, and he called for a medical timeout to take medication to ease his symptoms. Navone, ranked world No. 49 and never advancing past the second round at the US Open, held his nerve to take the first set in a tiebreak.
Cooler conditions under the Arthur Ashe Stadium roof briefly revitalized Djokovic, who fought back to level the match at one set apiece and even claimed a break lead in the third set — a position the legendary competitor has almost always turned into a comeback win throughout his career. But this time, Djokovic could not close out the match. As his health deteriorated further, Navone kept pressing, and the contest slipped away from the 39-year-old in the final two sets, culminating in a lopsided 6-1 fifth set that left the capacity crowd at Ashe Stadium stunned and somber.
It was in the final set that the emotion boiled over: Djokovic broke down in tears as the match slipped away, a raw display of disappointment few fans have seen from the notoriously tough competitor. After the final point, he mustered a smile to congratulate Navone on what will go down as one of the biggest upsets of his career, but could not hold back emotion as he walked back to the locker room, clearly distraught over the result.
The defeat ends Djokovic’s bid for a 25th Grand Slam singles title, which would have given him the outright all-time record, breaking a tie with Margaret Court. The tournament had been viewed as a strong opportunity for Djokovic, with world No. 1 Jannik Sinner sidelined by injury and defending champion Carlos Alcaraz returning from a long wrist layoff. This loss comes just two weeks after another shocking early exit to Argentine player Thiago Tirante at the Cincinnati Open, where Djokovic struggled in similar humid conditions.
After the match, Djokovic opened up about a long-standing “serious” health issue that has plagued him for years in high heat and humidity, causing vomiting, cramping and widespread muscle pain that left his body unable to compete. “It’s something that I have been carrying pretty much every match this year — vomiting, throwing up,” he told reporters. “And then my whole body starts to collapse basically, cramping and pain — the back just gave up in the end and shoulder, and I couldn’t close it out.”
The result has stoked long-simmering questions about Djokovic’s eventual retirement, questions the legend has repeatedly pushed back on. In a documentary released earlier this month, he insisted he has never placed an “expiry date” on his career, noting: “Why would I talk about retirement when I still keep proving to myself that I can still win?”
Despite the historic first-round exit and his ongoing health struggles, Djokovic says retirement is not on his immediate agenda. His priority, he says, remains finding a solution to the undiagnosed health issue that has disrupted his 2026 season, leaving his legendary career hanging in a rare moment of uncertainty.