World number one Dinara Safina suffered a shock defeat by France's Aravane Rezai at the Rogers Cup in Toronto.
The Russian won the first set 6-3 but her French opponent hit back to take the next two sets 6-2 6-4.
Top seed Safina was severely hampered by her serve, producing 17 double faults to give the world number 39 victory.
It follows yesterday's shock defeat of third seed Venus Williams by Kateryna Bondarenko.
Fourth seed Elena Dementieva, well placed in the absence of Safina and Williams, had a regulation 6-3 6-2 win over Japan's Ai Sugiyama.
Jelena Jankovic, ranked fifth, beat Patty Schnyder with a hard-fought 7-5 6-4 victory .
Seventh seed Vera Zvonareva beat Roberta Vinci 6-3 6-3 but number eight seed Caroline Wozniacki went crashing out to Jie Zheng, the Chinese woman winning 7-5 6-3.
Britain's Elena Baltacha went down 3-6 4-6 to former world number one Kim Clijsters.
Elsewhere Alisa Kleybanova beat Aleksandra Wozniak 6-4 6-4, Victoria Azarenka eased past Shuai Peng 6-3 6-3 and 12th seed Flavia Pennetta dispatched Maria Kirilenko by the same score.
In the day's other second round clash, Austria's Samantha Stosur ousted sixth seed Svetlana Kuznetsova in a commanding, if unexpected, 6-4 6-3 win.
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