Elina Svitolina vs. Johanna Konta
Svitolina is 3-0 against Konta at the tour level, though that record isn’t quite as one-sided as it appears. One of those matches went to 6-4 in the third set, and Konta won the first set of another, 6-1, before having to retire in the third. Whatever happened in the past, though, they’re both playing well now. Svitolina reached the semifinals at Wimbledon and has beaten three quality opponents at the Open—Venus Williams, Dayana Yastremska and Madison Keys—without surrendering a set. Konta is coming off one of the best and grittiest wins of her season, 7-5 in the third against No. 3 seed Karolina Pliskova. Either player could win this, but to do it, Konta would likely have to lift her game more than Svitolina would have to lift hers. Winner: Svitolina
Medvedev is in the middle of what the gentlemen of pro wrestling call a heel turn. Over the course of the last week, the Russian has taken on a new, villainous persona, goading the New York crowds to boo him, then claiming the energy helps him. I thought his act was funny the first time, and kinda contrived the second. Either way, it should make for good theater, if and when he debuts it in Ashe—if only this was during a night session.
The contest itself is exceedingly hard to call. They’ve met once, at Wimbledon in 2017, and Medvedev emerged a four-set winner. Medvedev has also had a much better summer, reaching the three straight finals and winning his first Masters 1000 in Cincinnati. At this point, he seems to have forgotten how to lose, and is able to solve any problem he faces on court, from opponents or fans. But Wawrinka could pose his toughest problem yet. He romped through his fourth-round match against Novak Djokovic, and hit the ball as cleanly as he has in two years. Will he have too much power for Medvedev, or will Medvedev find a way again? It should be fun finding out. Winner: Wawrinka
It has been a while since the man once known as Baby Federer launched an Oedipal—make that Fedipal—challenge at his tennis father. Their last two meetings, in 2017 and 2018, were routine straight-setters. Can he spring a surprise on Tuesday night? Dimitrov didn’t do much this summer until the Open, and in truth, he hasn’t faced a murderer’s row of opponents at Flushing Meadows; the best of them, Borna Coric, handed him a walkover. But Dimitrov wasn’t given that nickname for no reason, and he’s too talented not to return to something approaching the top of the game. But this would seem to be a leap too far, too fast. Winner: Federer
Serena Williams vs. Wang Qiang
Serena and Wang have never played, and a night match in Ashe is probably not the best place for Wang’s first meeting with the 23-time Grand Slam champ. But there are a few reasons to believe this might not be a blowout. Serena turned her ankle in her last match, and she hasn’t been able to shake off her injuries this year the way she once did. Wang is coming off a win over No. 2 seed Ash Barty, and more important, she plays an ultra-steady game that, on the right day, could give Serena fits. On the wrong day, of course, it could be batting practice. Winner: Williams
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