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Shahar Pe'er suffered a heartbreaking defeat in the second round of the $1,340,000 Kremlin Cup in Moscow on Thursday afternoon, losing 6-4, 6-7(4), 3-6, to world No. 7 Elena Dementieva after two hours and 35 minutes.
Pe'er (23) had a match point in the 12th game of the second set, but failed to take advantage of the chance and then lost the set on a tiebreaker.
The Israeli was unable to maintain her good form in the third and decisive set, which allowed Dementieva to take a 2-1 lead in their head-to-head meetings this year.
The 19-year-old Pe'er would have broken into the WTA top 20 for the first time had she won on Thursday, but will now need to wait until next week's Zurich Open for a chance to reach a new high in her young career.
Dementieva was still rusty from her recent thigh injury at the start of the match and gifted Pe'er the first game after double-faulting twice.
It wasn't long before the Israeli seized control of the set, cruising to a 5-1 lead. Dementieva slowly worked her way back into the match and won three straight games.
Pe'er twice missed set points in the eighth and ninth games, but closed out the set in the 10th game thanks to the Russian's unforced error. Dementieva had an awful 22 unforced errors in the first set, double the amount hit by the Israeli.
The Russian continued to improve at the start of the second set and it wasn't long before she had a commanding lead. Two consecutive love games gave Dementeiva a 4-1 advantage and she seemed to be on her way to tying the match. The Russian was two points away from winning the set in the seventh game, but Pe'er's resilience got her back into the set.
The Israeli reeled off four straight games and served for the match in the 12th game of the set. Pe'er had a 40-30 lead, but a good volley by Dementieva rescued match point and the set would ultimately go into a tiebreaker.
After taking a 3-0 lead at the start of the breaker, Pe'er dropped six straight points and after Dementieva took the tiebreaker, the match was knotted at one set each.
"When I managed to save a match point, I realized I could gear up my game," Dementieva said.
The Israeli won the first game of the decisive set, but Dementieva quickly took control and won four games in a row. Following the fifth game of the third set, Pe'er needed treatment for her lower back. After the five-minute break, she won the subsequent game.
However, the Israeli was unable to complete a comeback and Dementieva closed out the match in the ninth game of the set with a powerful backhand.
A little more than an hour after finishing her marathon singles match, Pe'er was back on court for a doubles quarterfinal match with partner Mara Santangelo.
The Israeli/Italian team defeated Slovakian Janette Husarova and Russian Elena Likhovtseva 6-4, 7-6(6) in 90 minutes, taking Pe'er's court time on Thursday to more than four hours.
Pe'er and Santangelo will play Czech Iveta Benesova and Russian Galina Voskoboeva in the semifinal. By reaching the last four, Pe'er has already guaranteed herself 135 ranking points that will take her into the world top 30 in the WTA doubles rankings.
AP contributed to this report.