Brandon Nakashima upset No. 1 seed Milos Raonic 5-7, 6-3, 7-6 (4) in the round of 16 at the Atlanta Open Wednesday at Atlantic Station.
Fourth-seeded Reilly Opelka beat Bjorn Fratangelo 7-6 (3), 7-6 (4).
Taylor Fritz and Jordan Thompson also won singles matches.
Fritz, the No. 5 seed, beat Steve Johnson 6-7 (5), 6-4, 6-1. Thompson defeated Peter Gojowczyk 7-6 (6), 6-4.
More results from tournament:
Men’s Doubles Round of 16
Matt Reid and Alexei Popyrin def. Frederik Nielsen and Andre Goransson 7-6 (4), 2-6, 11-9.
Ken Skupski and Luke Bambridge (1) def. Nicholas Monroe and Lloyd Glasspool 6-3, 6-7 (6), 10-6.
Benoit Paire and Treat Conrad Huey def. Harri Heliovaara and Emil Ruusuvuori 7-6 (2), 7-6 (2).
Matthew Ebden and John-Patrick Smith (4) def. Cameron Norrie and Taylor Fritz 6-2, 7-6 (1).