Daniil Medvedev vs Martin Damm — R32 — Winston-Salem Open

The No. 1 seed did not create a break, going 0 for 2 on break points and 0 for 10 in return games against a player ranked 87 places below him. Medvedev, now with three losses in his last five matches, ran into the geometry a 2.03-meter left-hander dictates: Damm held all 10 of his service games, won 30 of 36 first-serve points and saved both break points he faced. The one swing landed in game 8 of the second set, a break for 5-3. In 1h 22m the 22-year-old American booked a round-of-16 place and the best win by ranking of his career on record, past the No. 14 Tommy Paul he'd beaten at Miami in 2024.