Throughout the Western & Southern Open in Cincinnati, we'll preview the upcoming days' must-see matches.

Grigor Dimitrov vs. Juan Martin del Potro

One week you’re chest bumping each other in a doubles match in Montreal, and the next week you’re duking it out across the net in Cincinnati. Such is life on the pro tour. Del Potro and Dimitrov—two popular players, easygoing guys and good buddies—will face off in the day’s first match in the main stadium. Delpo, it turns out, is much friendlier with Dimitrov when they’re on the same side of the court than he is when they’re on opposite sides. The Argentine is 5-0 against the Bulgarian. Still, I’d say Dimitrov, who made the semis here last year, has a good shot of ending that streak on Thursday. With Roger Federer having pulled out of their quarter, this is an opportunity for two guys who have been waiting for one.

Winner: Del Potro

Garbiñe Muguruza vs. Madison Keys

The felt will fly in the second match in the big stadium. Muguruza and Keys are two of the WTA’s heaviest baseline hitters. They’ve each looked sharp in Cincy so far, and they each must be eyeing a title there with Serena Williams and now Angelique Kerber in absentia. Muguruza is a two-time Slam champ but, surprisingly, Keys leads their head to head 3-0. In those three matches, Muguruza has managed just one set.

Winner: Keys

John Isner vs. Frances Tiafoe

The two Americans have met just once, but it was a doozy. Last year at the U.S. Open, Isner came back from two sets to love to beat Tiafoe in a fifth-set tiebreaker in the brand new Grandstand. The setting may not be quite as grand—or the match quite as long—this time, but the stakes are still high. With the two top seeds in this section, Kei Nishikori and Alexander Zverev, out of the picture, Isner and Tiafoe have a chance at a Masters 1000 semifinal–or better. Tiafoe is coming off the win of his life, over Zverev, but Isner has been to the final here before, and I picked him to get back there again this year. So I’ll pick him in this one, too.

Winner: Isner

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What to Watch in Cincy: Delpo-Dimitrov, Muguruza-Keys, Isner-Tiafoe

What to Watch in Cincy: Delpo-Dimitrov, Muguruza-Keys, Isner-Tiafoe

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