Naomi Osaka's US Open look featured a warm-up jacket, a warm-up skirt, and many, many bows and ruffles.

Naomi Osaka vs. Karolina Muchova

Osaka was fortunate enough to get a wild card into the Open, but she hasn’t been handed the easiest draw. First up was 2017 Roland Garros champ Jelena Ostapenko, who Osaka knocked down with surprising ease. Her reward is a date with Muchova, the 2023 Roland Garros runner-up.

Game-wise, Muchova will present a very different challenge from the trigger-happy Ostapenko. The Czech has a variety of ways to win, and a variant of shots and spins she can use. She won’t give Osaka as much pace to work with, or the same look on every ball, the way Ostapenko did. She’ll also leave the baseline for the net, and force Osaka to do the same with her drop shots and angles.

The two have played twice, and split those two matches. Not surprisingly, Muchova’s win came on clay, and Osaka’s on the hard courts at Flushing Meadows in 2020. Both went three sets, and the rubber match should be competitive as well.

The most important question may be the simplest: Osaka played one of her best matches of the year against Ostapenko; can she maintain that level for another round? At her last three events—Wimbledon, Montreal and Cincinnati—she has won her first match and lost her second.

This time, I think Osaka will break out of that one-step-up, one-step-back streak. She likes these courts, and she likes the Open. She also tends to play up, or down, to her competition, and this competition is pretty high level. Winner: Osaka

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Sofia Kenin defeated 2021 US Open champion Emma Raducanu in the first round.

Sofia Kenin defeated 2021 US Open champion Emma Raducanu in the first round.

Jessica Pegula vs. Sofia Kenin

Pegula has a much higher ranking—No. 6 to No. 54—and a much better record over the past three years. During that time, she has been to six Grand Slam quarterfinals, including one at the US Open, while Kenin hasn’t made it out of the third round of any major. But Kenin does have the one thing both women want: a Grand Slam title, which she won in Australia in pre-pandemic January 2020. As for their head-to-head records, it stands at 2-2, though they haven’t met since 2021.

Based on their 2024 records, Pegula is a strong favorite. She’s 31-11, and Kenin is just 9-20. Pegula is also among the most in-form of WTA players at the moment, having just won Toronto and reached the final in Cincinnati. She’s hitting with a blend of depth, pace and consistency, and these fast courts do good things with her flat strokes.

That doesn’t mean we can count Kenin out. She obviously knows how to play on a Slam stage. Her win over Coco Gauff at Wimbledon last year shows that she cares about showing up against fellow Americans. And her win over Emma Raducanu on Tuesday night was a more impressive display of aggressive baseline tennis than we normally see from her. Kenin will be ready, but I’ll guess Pegula will be better. Winner: Pegula

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Jannik Sinner is looking to close out the Slam calendar the way he started it, with a grand trophy in his arms.

Jannik Sinner is looking to close out the Slam calendar the way he started it, with a grand trophy in his arms.

Jannik Sinner vs. Alex Michelsen

If you watch much tennis on TV in the States, it has been hard to miss Michelsen’s long, lanky presence this summer. The Californian is just 20, but it feels as if we’ve already seen a ton of him already. He made the final in Newport, the quarters in D.C., the final in Winston-Salem, and he came out of qualifying to reach the second round in Cincinnati. That work has put him into the Top 50 for the first time.

He has also run into Sinner in his travels. They played in Cincinnati, and the Italian won in two close sets, 6-4, 7-5. That match featured a lot of hard-hitting baseline rallies, and there wasn’t much between the two red-heads. Sinner broke in Michelsen’s opening service game, and then held out the first set; but Michelsen had his chances to break back. In the second, it was even until Sinner broke again at 5-5.

klchelsen made his 6’4 presence felt that day, and he will again in front of a home Open crowd. But best-of-five should give Sinner a little more room to breathe, and allow him not to panic if things don’t go his way early. Michelsen has the moxie to take a set, but three feels like a big ask right now. Winner: Sinner