Top seed Jelena Jankovic's US Open chances continued to dim with a listless 7-6, 6-3 loss to 75th-ranked Czech Iveta Benesova in her opening match at the Montreal Cup on Tuesday.
Jankovic's buildup has not inspired hope that the Serb will be making a return to the final this year with her play on hardcourts falling flat and concern over a nagging ankle injury mounting.
"I don't have any pain anymore, I just need to work hard on the practice court and work on getting better," Jankovic, runner-up at the 2008 U.S. Open, said. "I'm not where I would like to be.
"I have a week-and-a-half before the U.S. Open so hopefully I can prepare and play better there."
The loss marked the third consecutive hardcourt event that the world number three has made an early exit, having also fallen at the first hurdle in San Diego to Russian Alisa Kleybanova.
Prior to her injury, Jankovic had been enjoying a solid season highlighted by a win at Indian Wells. Her problems began after Wimbledon when she was forced to retire from a tournament in Slovenia.
Benesova, who had never won a match on Canadian hardcourts in two previous visits and had won only two matches on hardcourts this season, was not intimidated.
Jankovic, who showed no signs of an injured ankle, had looked in control, serving for the first set at 5-3.
But the Czech broke to get back on serve, forcing the set to a tiebreak which she dominated 7-3. Benesova broke in the second set on her way to a 3-0 lead. The Serb offered a brief fight back with a break in the fifth game but Benesova broke back to go up 5-3 and serve out the match.
Bopanna-Qureshi advance to 2nd round
Mason (USA): Rohan Bopanna and Aisam-ul-Haq Qureshi beat American Rajeev Ram and Bobby Reynolds to progress to the second round of the Western & Southern Financial Group Masters in Mason.
The unseeded Indo-Pak pair scored a 6-3, 1-6, 10-4 win over the wild card holder pair in the first round. They will next face eighth seeded Polish pair of Mariusz Fyrstenberg and Marcin Matkowski.
Third seeds Leander Paes and Czech Lukas Dlouhy will take on American Mardy Fish and Bahamas' Mark Knowles while fourth seeded pair of Mahesh Bhupathi and Max Mirnyi of Belarus are up against American combo of John Isner and Sam Querry.