Taylor Fritz has been playing some of his best tennis at the 2025 US Open. On Sunday, he cruised into the quarterfinals with a strong straight-set win over Tomas Machac. But waiting for him there is a very familiar—and very frustrating—challenge: Novak Djokovic.
Fritz has never beaten Djokovic in 10 tries. That’s right—0–10. And if he wants to win his first Grand Slam title (in what will be his 37th attempt), that streak has to end on Tuesday.
It’s a bit like watching Sisyphus push a boulder up a hill, only in Fritz’s case, he’s pushing two:
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Trying to win a Slam for the first time.
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Trying to beat Djokovic for the first time.
And, of course, one can’t happen without the other.
When they met at this same stage in New York two years ago, Djokovic dominated him: 6-1, 6-4, 6-4. Fritz has only managed to win three sets total across their 10 matches—all at the Australian Open.
“I think the first seven or eight times I played him, I probably just wasn’t good enough to have a real chance,” Fritz admitted after his win on Sunday.
What makes Djokovic such a nightmare opponent? According to Fritz, it’s the way Djokovic serves—especially his aggressive second serves—and how well he backs that up from the baseline. While Djokovic attacks Fritz’s serve with his legendary return, he doesn’t give Fritz the same opportunity in return games.
“He backs it up incredibly well with the serve,” Fritz said. “It’s tough to get on him the way he’s getting on you.”
Djokovic, for his part, knows what’s coming: aggression. It’s what he saw from Cameron Norrie last round, who had never beaten him either—and still hasn’t.
“I expect players that have never won against me to come out and try something different, to try and make me uncomfortable,” Djokovic said.
But tactics only go so far. Mentally, Fritz says playing Djokovic is just different. Against lower-ranked players, he can count on his opponents making mistakes eventually. Against Djokovic? You have to take the win.
“You’re playing someone who’s there for a reason,” Fritz said. “They’re not just going to hand it over to you. You have to go out and take it from them. I need to play more to win—and not to avoid losing, if that makes sense.”
That mindset showed in his fourth-round win. Fritz was calm, focused, and in control. But then Djokovic came out and played even better, dismantling Jan-Lennard Struff in straight sets.
Both men look sharp. Both are in quarterfinal form. But the history—and the pressure—heavily favor Djokovic.
If this weren’t a Slam…
If Djokovic wasn’t still chasing history…
If Fritz had come even close in recent matches…
Maybe, just maybe, he’d have a shot.
But as it stands? Fritz will need the match of his life—and a bit of belief—to finally push that boulder over the top.
