Nick Kyrgios came from a set down to beat world number one Daniil Medvedev at the Canadian Open, as Iga Swiatek won comfortably.
Women's world number one Swiatek comfortably reached the last 16 with a straight-set win over Ajla Tomljanovic.
The 21-year-old Pole, a two-time Grand Slam winner, won 6-1 6-2 and will play Brazil's Beatriz Haddad Maia next.
American great Serena Williams lost 6-2 6-4 to Swiss 12th seed Belinda Bencic in Toronto in her first match since the 23-time Grand Slam singles champion suggested she will retire from tennis.
Writing for Vogue, Williams said she will be "evolving away" from the sport after the US Open, which begins on 29 August.