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For the first time since 2002—twenty-two years ago—neither Novak Djokovic, Rafael Nadal nor Roger Federer will win a Grand Slam title.

That stunning fact was confirmed with a rather stunning result, as 28th seed Alexei Popyrin defeated Djokovic in the third round of the US Open, 6-4, 6-4, 2-6, 6-4.

Popyrin came into the match 1-11 against Top 5 players, but he also came into it having taken two sets off Djokovic at the majors this year. The Serbian superstar eventually pulled away at the Australian Open and Wimbledon, but it was a different story at Flushing Meadows.

Novak Djokovic never looked comfortable on Friday night.

Novak Djokovic never looked comfortable on Friday night.

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Djokovic came into the Open having not played a match since winning Olympic gold at Roland Garros. His last hard-court tournament was at Indian Wells, where he lost to unheralded Luca Nardi. Popyrin, meanwhile, won his first Masters 1000 title in Montreal, defeating Ben Shelton, Grigor Dimitrov, Hubert Hurkacz, Sebastian Korda and Andrey Rublev. As impressive as that list is, though, none of those players are a Grand Slam champion—let alone a 24-time major winner.

Popyrin had two things to lean on, though: fast strokes, and a fearless approach. He used those to great effect—none more so than when he broke Djokovic for 3-2 in the fourth set with a screaming winner, in every sense of the word:

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The 25-year-old, 6'5" Popyrin, who failed to serve out the match at 5-2 but did so two games later, is now into the fourth round of a Slam for the first time. He'll play Frances Tiafoe on Sunday.

As for Djokovic—who struck 14 double faults, his most ever in a Grand Slam match—he exits the US Open before the fourth round for the first time since 2006. He also leaves Queens with just one tournament win this year.

It was a big one, but despite his struggles in 2024, this remains a big loss.

TENNIS.com will have additional coverage of this match from Steve Tignor.