Naomi Osaka vs. Olga Danilovic

On paper, this doesn’t look like danger time for the third-seeded Osaka. She may not have been firing on all cylinders, exactly, in her opening-round win, but she was firing too hard for her opponent, Marie Bouzkova. Danilovic is ranked No. 145; that’s 58 spots lower than Bouzkova. And she had to qualify for the main draw at this event. But Danilovic is also a fairly unknown quantity. She’s just 20, she’s 6-feet tall, she’s a lefty, and Osaka has never faced her. She was also good enough to beat Petra Martic at the Australian Open earlier this year for her first win at a major tournament. So if Osaka is misfiring, which is always possible, surprises could be in store.

But I wouldn’t bet on it. Few players in either draw are as comfortable on US Open show courts as Osaka. Winner: Osaka

>>> Editor's Note: On Wednesday morning, Danilovic withdrew from the US Open due to "a medical reason," per the tournament.

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After reliving her 2017 win in New York over Madison Keys, Stephens is in a great spot come Wednesday.

After reliving her 2017 win in New York over Madison Keys, Stephens is in a great spot come Wednesday. 

Coco Gauff vs. Sloane Stephens

At 28, with Serena Williams out of the draw, Stephens—like it or not—finds herself as a senior member of the U.S. women’s contingent. If that doesn’t make her feel her age, facing the 17-year-old Gauff surely will. These two African-American stars have never played; what they won’t offer is a stark contrast in styles. Each has easy power on their serves and ground strokes, each plays excellent defense, and each thrives on long rallies and physical points—there should be some great ones over the course of this match. Gauff and Stephens also both survived scares in their openers—Sloane against Madison Keys, Coco against Magda Linette.

If you go by recent form, Gauff should be the favorite here; she’s ranked 43 spots ahead of Stephens. But Sloane, the 2017 champion, tends to raise her game in New York. Winner: Stephens

Medvedev feels at home on Arthur Ashe Stadium.

Medvedev feels at home on Arthur Ashe Stadium. 

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Daniil Medvedev vs. Dominik Koepfer

Medvedev had little trouble grinding down Richard Gasquet in the first round. If you go strictly by Koepfer’s ranking, No. 57, it would seem like the Russian is in for another straight-set cruise on Wednesday night. But Koepfer was also one of Medvedev’s opponents during his infamous, villainous run at Flushing Meadows in 2019. That time, the German-turned-Floridian pushed Medvedev to a fourth-set tiebreaker in a raucous Armstrong Stadium, and pushed him to the brink mentally.

Koepfer is a lefty with a lot of spin and a lot of grit. If Medvedev can make quick work of him as well, we’ll know he’s in good form. Winner: Medvedev