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Iga Swiatek vs. Naomi Osaka

It feels like a long time ago when these two were Instagram buddies during the pandemic, doesn’t it? In those days, Osaka was the WTA's brightest young star, and the new face of women’s tennis, while Swiatek was one up-and-comer among many. Now, of course, it’s Iga who is firmly established at No. 1, and Osaka who is ranked 134th and working hard to put back-to-back wins together.

They’ve played twice. In the Before Times, Osaka beat Swiatek in two close sets in Toronto in 2019. In the post-COVID era, Swiatek rolled past Osaka 6-4, 6-0 in the 2022 Miami final. Right now, each of them has four major titles to her name, but that’s hardly a sign that they’ll be evenly matched on Wednesday. Three of Swiatek’s Slam wins have come at Roland Garros, while Osaka has never been past the third round here, or reached the final of any clay-court event.

Should we expect Swiatek to steam past Osaka the way she does just about everyone else on dirt, and the way she did against her in Miami? It’s possible. Iga is a lot more confident right now, and a lot more comfortable on clay. At the same time, Osaka does have more weapons than most of Swiatek’s opponents, and a more powerful return of serve, which should give her a chance to take control of some of the rallies from her. The trick for Osaka may be doing that and ending the point, before she can sabotage herself with an unforced error. Winner: Swiatek

Tune in to Tennis Channel.

Tune in to Tennis Channel.

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Jannik Sinner vs. Richard Gasquet

Every metric favors Sinner. He’s 22; Gasquet is 37. He’s ranked No. 2; Gasquet is No. 124. He’s 29-2 on the season; Gasquet is 3-8. He won a major title this year in Australia; Gasquet hasn’t made it past the third round at a Slam, any Slam, since 2016. In their two previous meetings, Sinner won both times. Sinner hits with huge pace from both sides, something that will probably force Gasquet to move back so he has enough time for his long, loopy ground strokes.

Gasquet will have two things going for him, neither of which is measurable by numbers. (1) Sinner recently suffered a hip injury that kept him off the court for a couple of weeks leading into this tournament. He says it felt good after his first-round match, but that’s not ideal preparation. (2) Gasquet will have the backing of the crowd, who should buoy him if he falls behind early. Still, while the atmosphere should add entertainment value, it probably won’t be enough to close the gap between these two. Winner: Sinner

Gasquet will need more than just the crowd in order to hang with Sinner.

Gasquet will need more than just the crowd in order to hang with Sinner.

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Frances Tiafoe vs. Denis Shapovalov

One is a right-handed American, the other is a left-handed Canadian, but otherwise there are a lot of similarities between these two mid-20 veterans. Both are flashy, streaky, athletic shot-makers who have made themselves consistent enough to reach the Top 10. But no farther—No. 10 is the career-high for both. Neither stayed there for long, either. Their streakiness returned, and they slid back down the rankings. Shapovalov is currently ranked 118th and has a 7-13 record in 2024, while Tiafoe is 26th and 11-11 this season.

Put these two across from each other and you should see an explosive, emotional, unpredictable, imperfect, back-and-forth affair. While Tiafoe has the higher ranking, Shapovalov leads their head-to-head 4-2 (they haven’t faced each other since 2021). In the first round, Shapo won in three, and Tiafoe won in five, but even with his relative lack of efficiency, I’ll take the American here. Winner: Tiafoe