Three to See, US Open Day 4: Andrey Rublev has his work cut out for him against Gael Monfils

WATCH: Is Andrey Rublev a US Open sleeper?

Andy Murray vs. Grigor Dimitrov

Like Kvitova vs. Wozniacki on the women’s side, this match feels like a throwback to the 2010s. To 2016, to be exact, which is the last time that the 36-year-old Brit and the 32-year-old Bulgarian faced each other. From 2011 to 2016, they played 11 times; Murray won eight of them, and two of three at the majors.

Dimitrov is younger and higher-ranked—No. 19 to Murray’s 37. He has also had a sneaky-good Grand Slam season, reaching the fourth round at Roland Garros and Wimbledon. Murray, meanwhile, has been nursing an ab injury through much of the summer.

But on this day, it may actually be the elder Murray who has the physical advantage. He advanced in straight sets in the first round, and looked good doing it, against Corentin Moutet. At the same time, Dimitrov was slugging his way through a marathon five-setter with Alex Molcan. Dimitrov saved match points and finally won it 11-9 in a deciding tiebreaker. When it was over, he looked a little shaken.

Can he bounce back in time to grind away with Murray? It’s a big ask, no matter what kind of form he’s in. Winner: Murray

Andrey Rublev vs. Gael Monfils

The 25-year-old Rublev and the 36-year-old Monfils come from different ATP generations, but they play a similar role within them. They’re the guys everyone likes, who don’t play mind games in matches, who are good sports and good losers. They’re also, perhaps not coincidentally, the guys who don’t end up winning the big events.

The Russian and the Frenchman have played twice, and each has won once. For their third meeting, the eighth-ranked Rublev will be a solid favorite over his 162nd-ranked opponent. But it’s actually Monfils who has had the better summer. He went 7-4 at four US Open tune-ups, and showed that he has lost little of his acrobatic ability, while Rublev went out in the first round in Toronto and Cincinnati.

This could be a long one, and an entertainingly sporting one—but it’s still one that Rublev, who has reached the quarters at two majors this year, should win. Winner: Rublev

Daria Kasatkina vs. Sofia Kenin

The Russian and the American could go on a while. They’re both 5’7”, and neither has a reliable way to blow the ball past the other. Thus they’re both dedicated to the rally, the grind, and the art of point construction. They’ve played three times; Kenin has won twice, both times in three sets.

Kasatkina is currently ranked 14th to Kenin’s 101. Kenin has been ever-so-slowly been improving her position; she won a total of five matches at Wimbledon, including qualifying. Kasatkina has been holding steady this summer, reaching a final in Eastbourne, and a quarterfinal in Montreal. Each woman has had a signature moment of late: Kenin’s came in a win over Coco Gauff at Wimbledon; Kasatkina’s came in a loss, at 3 a.m. in Montreal, to Elena Rybakina. Maybe the winner of her signature moment wins again. Winner: Kenin