Novak Djokovic faced an unexpected and challenging first-round defeat at the 2026 U.S. Open, losing to Argentina’s Mariano Navone after a grueling five-set match lasting 4 hours and 36 minutes. The 39-year-old Serbian star, a 24-time major champion and No. 4 seed, struggled visibly on court with stomach issues, throwing up multiple times and even using an inhaler. This defeat marked the first time since 2006 that Djokovic exited a major tournament in the opening round, ending a flawless 19-0 U.S. Open first-round record.

The match took place on a humid evening under the closed roof of Arthur Ashe Stadium, where Djokovic’s physical struggles were evident from early on. Despite showing flashes of his former self, including a comeback to even the match at one set apiece, the persistent discomfort ultimately overwhelmed him in the latter sets. His opponent Navone, ranked No. 49 and yet to win an ATP Tour title, seized the moment to claim a stunning upset, a victory he called a dream come true against the legendary “GOAT.”

Djokovic acknowledged his health challenges after the match, remarking that playing felt unbearable and that he “despised every moment” on court. He is grappling with a long-standing medical condition he mentioned weeks earlier, complicating his quest to remain competitive at the highest level. The loss means Djokovic will drop out of the top 10 rankings for the first time since mid-2018, reflecting a turning point in the career of one of tennis’s greatest players.

The absence of Djokovic, along with Roger Federer and Rafael Nadal, from the second week of a major is a rare occurrence, last seen at the 2003 Roland Garros. Tennis analyst John McEnroe commented on the situation, emphasizing that this moment highlights Djokovic's humanity and underscores the magnitude of his past accomplishments. Meanwhile, Navone celebrated his breakthrough performance on an iconic stage, illustrating the unpredictable nature of professional sports.