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Ben Shelton vs. Jannik Sinner

Shelton is looking to end Sinner’s 17-match win streak, and the American may have as good a chance as anyone—which still might not be a lot, considering the Italian's imperious form. That said, Shelton owns a win over Sinner, and it happened just a few months ago. That also took place in the fourth round of a hard-court Masters event, in Shanghai. They met again, that same month, in Vienna, and Shelton couldn’t break Sinner’s serve. Both players will fight through to the very last point, and the rubber match is worthy its nighttime billing. Winner: Sinner

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Shelton is the only American remaining on his half of the draw.

Shelton is the only American remaining on his half of the draw.

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Alexander Zverev vs. Alex de Minaur

The Australian has been a talking point of the 2024 season for good reason, from breaking into the Top 10 to sharing a championship weekend with girlfriend Katie Boulter. Since entering his spotlight era, de Minaur has had no problems at Indian Wells, winning sets 6-1, 6-2, 6-0 and 7-5. Making it to the quarterfinals likely won’t be as straightforward, however, since he’s lost to Zverev six times in their eight meetings. Speaking of Zverev, ever since his return from the 2022 injury, his game has flown under the radar. If anyone can take the spotlight away from de Minaur, and onto himself it’s Zverev. Winner: Zverev

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Angelique Kerber vs. Caroline Wozniacki

A battle for the ages is bringing the heat to Indian Wells. Two returning, fan-favorite moms are going head-to-head for the 16th time, with their last face off in 2018. Their last match at the BNP Paribas Open was even farther back, in the 2013 semis. Both players are well outside the Top 100, but it won't feel that way tonight, when these friends and competitors give the crowd a show. Winner: Wozniacki