Upsets bookended the Rogers Cup on Monday with Ukrainian teen Dayana Yastremska beating British 13th seed Johanna Konta 6-3 6-2 early on in Toronto before Maria Sharapova fell 4-6 6-3 6-4 to Anett Kontaveit under the lights in the evening session.
The Russian sent a forehand service return long on match point to end the engrossing two hour and 41 minute battle.
Kontaveit will next face either seven-time Grand Slam champion Venus Williams or Spain’s Carla Suarez Navarro, who play their first-round match on Tuesday.
Earlier in the day, Yastremska, ranked 33rd in the world, squandered four match points but took her fifth opportunity, dispatching Konta with the clock barely ticking past noon on the Toronto hardcourt.
The result avenged Yastremska’s loss to Konta when the pair met at Eastbourne in June.