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WATCH: Medvedev speaks to the press after winning his first match as world No. 1.

Daniil Medvedev vs. Gaël Monfils

If you’re a fan of contrasts in style, this is a match-up for you. Medvedev is a 26-year-old artist-grinder, while Monfils is a 35-year-old athlete-acrobat. But below those obvious differences, the Russian and the Frenchman are both long and fast and can cover an immense amount of ground between them, and both like to keep their opponents guessing with their shot selection. They’ve played twice, both times on hard courts in 2019, and each has won once. Monfils may be the crowd favorite on Monday, but Medvedev, who could be No. 1 in the world for years to come, is the favorite on court. Winner: Medvedev

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Fernandez is fresh off winning her second career WTA title in Monterrey.

Fernandez is fresh off winning her second career WTA title in Monterrey.

Leylah Fernandez vs. Shelby Rogers

Here we’ll see the third meeting between two fan favorites from last year’s US Open. Fernandez made the final at Flushing Meadows, while Rogers knocked out top seed Ashleigh Barty. We’ll also see a rematch of their fourth-round contest from Indian Wells last fall. Rogers won that one in a third-set tiebreaker, and she won their only other meeting, also on hard courts, in Lexington in 2020. Rogers is not unlike Fernandez’s last opponent, Amanda Anisimova—tall, powerful, and not a defensive specialist. Anisimova overpowered Fernandez for most of two sets, and held match points, before the stubborn Canadian found a way to survive the second set, and Anisimova retired. Rogers, meanwhile, has been just as clutch in her wins over Nuria Parrizas Diaz and Jelena Ostapenko. This contest between puncher vs. counterpuncher should be a close one as well. Winner: Fernandez

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Stefanos Tsitsipas vs. Jenson Brooksby

Brooksby’s ceiling seems to get higher by the month. In Acapulco, he came a shot or two away from beating Alexander Zverev, and on Saturday he made stunningly quick work of 25th seed Karen Khachanov, 6-0, 6-3. Can the 21-year-old Californian’s unorthodox style, with its changes in speeds and spins, work the same kind of disruptive magic against the fifth-seeded Tsitsipas? Can he find a way to exploit the Greek’s weaker backhand side? Tsitsipas barely found his way past another American with a very different style, Jack Sock, in the last round. Brooksby may not as generous as Sock was when the match was on the line. Winner: Brooksby

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