In the men’s draw in Toronto, Alexander Zverev set up a fourth-round tie against Francisco Cerundolo with a 6-7 (5-7) 6-3 6-2 win against Italy’s Matteo Arnaldi.
The victory was the German’s 500th tour-level win of his career.
“It’s a great achievement. There’s not a lot of players that reached that milestone,” Zverev said.
“Of course I still want 500 more hopefully to come, and maybe even more.
“When you start your career, you wish to play on tour, you wish to have a successful career, win as many matches as possible.”
Former world number one Daniil Medvedev was knocked out by defending champion Alexei Popyrin.
The Australian overcame the Russian 10th seed with a 5-7 6-4 6-4 victory to book a tie with fifth seed Holger Rune in the next round.
“I felt like I should have won that first set,” said Popyrin, who led Medvedev 4-2 before losing the opening set.
“I was in the driver’s seat, I felt like I was really comfortable out there, and then something happened.
“I kind of let go and I started feeling my shots a little bit. When that happens, when you play a fast pace against him, he starts feeling the ball a little bit more.”
Third seed Lorenzo Musetti crashed out of the tournament after the Italian was beaten 3-6 7-6 (7-4) 6-4 by 26th seed Alex Michelsen of the United States in the third round.
Michelsen’s win sets up an all-American clash in the fourth round where he could face either Learner Tien or Reilly Opelka.
Eighth seed Casper Ruud also reached the fourth round with a 7-6 6-4 win against Nuno Borges and will face 11th seed Karen Khachanov, who overcame Emilio Nava 6-7 6-4 6-1.
Argentina’s Francisco Cerundolo got the better of compatriot Tomas Martin Etcheverry in straight sets and will face either top seed Alexander Zverev or Matteo Arnaldi in the next stage.