Novak Djokovic suffered a 7-6, 5-7, 4-6, 6-2, 6-1 defeat to Mariano Navone at the US Open, the first time he had fallen in the first round at a Grand Slam in 20 years.
The match against Navone was Djokovic's longest first-round match of his career, lasting four hours, 35 minutes.
The former World No 1 took a medical time-out before the start of the fifth and final set.
Djokovic repeatedly vomited during the match and required treatment from the medical team after the fourth set.
The Serb appeared increasingly distressed as the contest entered its decisive stages.
Battling hot and humid conditions, Djokovic visibly struggled to regulate his body temperature, leaning heavily on ice packs around his neck and head during changeovers.
As Navone moved 4-1 ahead in the final set, 24-time Grand Slam winner Djokovic broke down in tears. Despite attempting to fight his way back into the contest, Djokovic ultimately suffered a dramatic five-set defeat.
As Djokovic left the court, the crowd at the Arthur Ashe Stadium stood on its feet and thanked the 39-year-old for the way he fought against Argentine Navone.
It was the 24-time Grand Slam winner Djokovic's first defeat in the first round of a major since losing at the same stage of the 2026 Australian Open.
Navone, the world No 49 who grew up idolising Djokovic, was in shock after pulling off the biggest win of his career.
“It is the best day I’ve had. It’s amazing - and on one of the biggest stages,” Navone said post-match.
“The way we played; five sets against the GOAT. It doesn’t happen every day.
“I am very happy. I don’t know what I can say.”
“It is unbelievable,” he continued.
“It means a lot for me ... the match was tough for me because you are playing with the GOAT. It is a dream come true, 100 per cent.”
