Brit Johanna Konta failed to advance to the next round of the 2017 Rogers Cup after losing to Russian Ekaterina Makarova in Toronto.
Ekaterina Makorava beat Konta 2-1 winning 5-7 7-6 (7-4) 6-3 and will take on Lucie Safarova in the next round.
Elsewhere, World number one and Czech Republican Karolina Pliskova won her first game after returning to the top of the WTA rankings.
Pliskova beat Anastasia Pavlyuchenkova from Russia in straight sets of 6-3 6-3 to reach the next round.
The 25-year old played her first game since losing at the second round at Wimbledon.
She said after the game; “I had a little bit (of nerves) before the match but during the match I felt much better, especially at the end”.
“I think it was not the best tennis from my side but I was trying to improve in the match”.
In other events, Wimbledon champion Garbine Muguruza advanced to the next round after beating Kirsten Flipkens of Belgium in straight sets of 7-5 6-2.
The Spaniard who was playing her first games since beating Venus Williams at the 2017 Wimbledon final will look forward to adding the Rogers Cup to her silverware.
American and 18 year old Cici Bellis also made it to the next round after beating Russian Svetlana Kuznetsova in straight sets of 6-4 7-5.
There were also wins for Wimbledon finalist Venus Williams as she eased past Katerina Siniakova in straight sets. The American won 7-5 7-5 with Simona Halep also making it to the next stage with straight set win of 6-3 6-4 over Slovak Magdalena Rybarikova.
Lastly, there were wins for former World number one Angelique Kerber who eased past Croat Donna Vekic 6-4 7-6 (7-5) and Petra Kvitova knocking off Sloane Stephens 7-6 (7-4) 3-6 6-2.