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Pless will now face Frenchman Paul-Henri Mathieu, who beat Sweden's Jonas Bjorkman 7-5 6-4.
BBC: Kuerten edges out Safin
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Second seed Guillermo Coria stormed into the third round with a 7-6 6-3 win over France's Paul-Henri Mathieu.
BBC: Nadal maintains form
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French qualifier Paul-Henri Mathieu produced a stunning comeback to claim the Kremlin Cup with victory over Sjeng Schalken.
BBC: Mathieu claims shock win
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The Spaniard thrashed Russian 27th seed Mikhail Youzhny 6-0 6-2 6-2 to set up a clash with compatriot Marcel Granollers, who beat a tired Paul-Henri Mathieu.
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Defending Olympic champion Nicolas Massu of Chile was dumped out by number seven seed David Nalbandian, while Russian fourth seed Nikolay Davydenko went down 7-5 6-3 to Paul-Henri Mathieu.
CNN: Federer, Nadal and Djokovic cruise through
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But despite conceding three successive games, Federer rallied to take the first set and after just one hour and 41 minutes he had booked a third-round spot against Paul-Henri Mathieu , who overcame French compatriot Guillaume Rufin 7-6 (7-3) 6-4 6-3.
BBC: Roger Federer wins at US Open as Davydenko & Cilic lose
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Two years after winning the longest match in grand slam history, No.10 John Isner was at it again as he faced France's Paul Henri-Mathieu in a marathon encounter.
CNN: Nadal cruises as Murray battles back at French Open