Is this Taylor Fritz's best chance to beat Novak Djokovic for the first time?

NEW YORK—Here comes Sisyphus pushing his ball back up the hill. Can he get it over the top this time?

I’m referring to Taylor Fritz, tennis’ version of that symbol of eternal frustration. In this case, the American will be pushing two balls up two very steep hills: (1) He’s trying to win his first Grand Slam title in his 37th attempt, and end a 22-year drought for U.S. men; and (2) He’s trying to get his first win over Novak Djokovic in their 11th encounter.

No. 1 obviously can’t happen if he doesn’t succeed at No. 2, which will happen in the quarterfinals on Tuesday.

What explains the extent of Fritz’s futility? In their previous 10 matches, which date back to 2019, he has managed to win just three sets, all at the Australian Open. When they played in this round in New York two years ago, Djokovic blitzed him, 6-1, 6-4, 6-4.

Fritz admits that it took him a long time just to feel like he was in the same league as the Serb.

“I think the first, almost like seven or eight times I played him, I probably just wasn’t a good-enough player to really have that much of a chance,” Fritz said on Sunday night.

I need to play more to win and not to lose, if that statement makes sense. Taylor Fritz

For Fritz, the biggest difference-maker, shot-wise, is Djokovic’s second serve. He can attack Fritz’s serve with his great return, but he doesn’t let Fritz do the same to him.

“I think what makes it tough is he serves well, he serves aggressive on second serves,” he said. “It’s tough to take advantage of his serve for how well he also returns and just is from the baseline.”

“He backs it up incredibly well with the serve. So it’s tough to sometimes get on him the way that he’s, I guess, getting on you with the return.”

For his part, Djokovic expects Fritz to up his aggression level. He’s already seen something similar from Cam Norrie, who was 0-6 against Djokovic—and is now 0-7.

“That was the case with Norrie, actually, last round,” Djokovic said. “I mean, he was playing more aggressively than he has ever played against me. So that’s something I expect. I expect players that never won against me to come out on the court and try something different and try to make me feel maybe uncomfortable and play more aggressive.”

Maybe more important than any one shot or tactic is how they match up mentally. For Fritz, playing Djokovic is still different from playing just about anyone else, other than perhaps Carlos Alcaraz and Jannik Sinner. Against lower-ranked players, Fritz says he can trust that if he stays in there, his opponents “will kind of give it to me or they’ll make mistakes.”

“But against the top guys…because you’re playing someone who they're where they’re at for a reason, they’re not just going to hand it over to you, they're not just going to give you a random mistake on a big point,” Fritz says. “You have to maybe pull the trigger and go out and take it from them.”

“I need to play more to win and not to lose, if that statement makes sense.”

Is Fritz in the right place to make that happen? Watching his straight-set fourth-round win over Tomas Machac, one would think so. But then, as he likes to do to the younger American, Djokovic one-upped him. He went out and was, if anything, even more impressive in his own straight-set win, over Jan-Lennard Struff. As far as their level goes, Fritz and Djokovic have both played themselves into Grand Slam quarterfinal—i.e., top or near-top—form.

If this weren’t a Slam, if Djokovic wasn’t trying to win one more major before he retires, if he had shown any signs of slippage against guys not named Alcaraz or Sinner, I’d say he’s finally vulnerable to Fritz.

If Fritz had come close recently, if he had a game that he could raise to substantially higher levels on certain nights, if Djokovic’s best shot, his return, wasn’t such a perfect match for Fritz’s best shot, his serve: I’d say Fritz had a puncher’s chance, at home, of getting win No. 1.

But none of those things are true. Winner: Djokovic