Daniil Medvedev can deny Novak Djokovic another crack at history at U.S. Open

Sunday will mark the second time Novak Djokovic has stared down history and seen Daniil Medvedev standing in the way instead.

The first time — the 2021 U.S. Open final — resulted in tears.

Djokovic was attempting to become the first player since Steffi Graff in 1988 to win a calendar year Grand Slam and he was instead stymied by the quirky Russian in straight sets. By the third set, Djokovic was crying into a towel and by the end, Medvedev had won his first —and only — Grand Slam title.

Thanks to Medvedev’s stunning upset over No. 1 Carlos Alcaraz Friday, Djokovic will either earn his redemption or lose a shot at another milestone — this one, matching Margaret Court’s all-time record of 24 Grand Slam titles in the Open era.

“I’m aware of it, and of course I’m very proud of it, but I don’t have much time nor do I allow myself to reflect on these things,” Djokovic said Friday after dispatching American Ben Shelton, 6-3, 6-2, 7-6 (4). “When I did that in the past, like [in the] ’21 finals here, I was maybe overwhelmed with the occasion and the opportunity and I underperformed. I don’t want this to happen again.”

And despite everyone clamoring for a Djokovic-Alcaraz Wimbledon final rematch, the third-seeded Russian is a force.

Off the court, he is outspoken and wry. On it, he’s an unorthodox player, boasts an effective slice serve, and is one of the best returners in the game. He thrives on hard-court surfaces, uses his 6-6 frame efficiently, plays with pace, covers the court with speed and is the opposite of risk averse.

He is, in short, a handful.

But Djokovic is the best — possibly the best ever. And Medvedev understands what that means: Prior to his win over the Serbian at the Dubai Tennis Championships in March, Medvedev had lost four straight to Djokovic. He’s 5-9 all time against him.

“Novak, when he loses, he’s never the same after,” Medvedev said. “He’s always better than the previous time he plays….