Roman Safiullin vs Hugo Grenier — R64 — Winston-Salem Open

Seven weeks after taking a set off Djokovic in the Wimbledon round of 16, Safiullin lost his first match back to a lucky loser ranked 258th. The favorite converted three of his four break chances and still finished 92-106 down in points, undone by Grenier's 14 aces and 77 percent of first-serve points won. The third set decided it: Safiullin won 45 percent of his first-serve points there against 86, and the lucky loser broke back in game 6 for 3-3, then again in game 8 for 5-3. The win, in 2 hours 18 minutes, ends a five-match losing run on record for Grenier, whose last one came at the Qatar Open in February 2024, and sends him into the last 32 at the Winston-Salem Open.