Keys, a runner-up at the 2016 tournament in Montreal, matched Ana Ivanovic for the longest gap between quarterfinal appearances at the event in the Open Era. Keys had not made it past the second round in Canada since losing to Simona Halep in that final nine years ago.

No. 2 seed Iga Swiatek was taken out by Clara Tauson in the fourth round, but there are still four very dangerous contenders looking to reach the final from the bottom half at WTA Toronto.