Top seed and home favourite Marat Safin was bundled out of the Kremlin Cup, losing to unseeded Czech Radek Stepanek 7-6 4-6 6-3 in the second round on Wednesday.
The former world number one, who survived a first-round scare against his doubles partner Max Mirnyi on Monday, finally ran out of steam against 74th-ranked Stepanek.
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The defeat dented Safin's chances of qualifying for the year-ending Tennis Master Cup in Houston, but the 2000 U.S. Open champion was still optimistic.
"I still have three tournaments left in Madrid, St Petersburg and Paris, so I think I have a good chance," said Safin, who is trying to regain his old form this season after an injury-plagued 2003.
Safin's Davis Cup team mate, Igor Andreev, started the day well for the Russians as he upset fourth-seeded American Vincent Spadea 6-4 4-6 6-4
Eight-seeded Russian Nikolai Davydenko advanced to the quarter-finals with a 6-2 6-4 victory over last year's Kremlin Cup finalist Sargis Sargsian of Armenia.
Second seed Joachim Johansson of Sweden also moved safely into the last eight, beating unseeded Frenchman Cyril Saulnier by the same score.
Italy's seventh seed Filippo Volandri edged Swede Robin Soderling 3-6 6-1 7-6 in a first-round battle between two of the hottest players on the tour.
Volandri, who meets Britain's Greg Rusedski next, earned the ATP Player of the Month honours for September while Soderling won his first title last Sunday in Lyon.
BRUSHED ASIDE
On the women's side, Svetlana Kuznetsova brushed aside Czech qualifier Michaela Pastikova 6-2 6-2 to set up a possible quarter-final meeting with fellow Russian Elena Dementieva, who she beat in last month's U.S. Open final to win her first grand slam title.
"It would be nice to face Elena once again, even though the centre court is a bit slower here than it was in New York," fourth-seeded Kuznetsova said. "It may give Elena a bit of an edge because I won't be able to hit so many winners against her this time."
Dementieva takes on Croatian qualifier Sandra Mamic, who crushed former French and Australian Open champion Mary Pierce on Tuesday, in her second round match on Thursday.
Earlier, Dinara Safina outlasted Anna Chakvetadze 6-4 1-6 6-3 in a see-saw first-round clash between two Russian teenagers and will now face world number two Lindsay Davenport.
The American could regain the world's top spot from Amelie Mauresmo if she beats Marat Safin's younger sister in a second-round match on Thursday.
France's Mauresmo withdrew from the $2.3 million tournament in Moscow after injuring her left thigh in Sunday's Grand Prix final in Filderstadt against Davenport.
