Laura Robson lost to a woman 24 years her senior as she went out in the opening round of the Japan Open.
The paths to the US Open women's semi-finals to be played on Friday at the US National Tennis Center in Flushing Meadows.
Victoria Azarenka charged into the third round of the US Open with a 6-3 6-1 win over Canada's Aleksandra Wozniak.
Order of play for day four of the US Open, with Rafa Nadal, Roger Federer, Serena Williams and Victoria Azarenka all on court.
The seeds continued to tumble out of the WTA Quebec event as Aleksandra Wozniak and Petra Martic became the latest casualties.
Round-up: Laura Robson produced the performance of her career to beat Kim Clijsters while Victoria Azarenka rolled into the third round.
Round-up: Jelena Jankovic marched into the semi-finals of the Texas Open with a comfortable 6-2 6-1 win over Sorana Cirstea.
Round-up: Australia's Casey Dellacqua stunned fourth seed Yanina Wickmayer 6-4 6-3 to move into the quarter-finals of the Texas Open.
A former world number one and two Grand Slam champions enjoyed routine quarter-final victories to stay on course in Montreal.
Petra Kvitova returned to her best during a Montreal Cup that has been dogged by rain and the withdrawal of Victoria Azarenka.
Ana Ivanovic had a humbling start to her North American hard court campaign as the Serb one lost 6-0 6-0 to Roberta Vinci in Montreal.
Victoria Azarenka will play her first match since the London Games at the Montreal Cup with only one threat to her No.1 status in the draw.
France's Jo-Wilfried Tsonga finally overcame Canadian Milos Raonic 6-3 3-6 25-23 in the longest three-set match in Olympic tennis history.
Andy Murray reached the third round of the London 2012 singles after beating Jarkko Nieminen, and was given a mixed doubles wildcard.
ATP World Tour Finals
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