The 16th-seed Nicolas Almagro became the first seeded player knocked out from Shanghai Masters on Sunday, succumbing 6-2, 5-7, 6-7(3) to his opponent Alexandr Dolgopolov of Ukraine.
The 25-year-old Spaniard was the winner of the two's first and only meeting 3-0, but Dolgopolov, who lost more than half of his matches in 2010, organized a thrilling fight back to clinch the victory of the second.
Almagro broke twice to wrap up the first set 6-2, but he double faulted three times to lose the second set 5-7. Dolgopolov improved his serves in the third set, powering five aces to claim the match 7-6(3).
Tommy Robredo of Spain enjoyed a much easier game. The 28-year-old breezed past his compatriot AlberMontanes 6-3, 7-6(4) to advance into the second round.
Li Zhe, the only local player left in the qualifying matches, suffered a 2-6, 6-4, 6-7(7) defeat from Poland's Lukasz Kubot.
Saving five match points, the 69th-ranked Pole grabbed himself a berth at the tournament.
Kubot could have ended the match in a much easier way, but his dropped serve when he led 5-4 in the third set, enabling Li to battle back from an almost hopeless situation.
Li conceded the first set 2-6. However, the world number 520 seized the second set 6-4 to draw the score back.
After breaking Kubot to level the score to 5-5 in the third set, Li succeeded in bringing the match into tiebreak, in which he established a 6-2 lead.
Kubot refused to surrender. He survived four straight match points to get to 6-6 and finally ended the tiebreak 9-7.
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