Pless gave him a piece of cardboard with his name written in magic marker.
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Pless will now face Frenchman Paul-Henri Mathieu, who beat Sweden's Jonas Bjorkman 7-5 6-4.
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Denmark's Kristian Pless enjoyed a surprise 6-3 6-1 win over local hero Nicolas Escude in their quarter-final.
Federer was joined in the second round by Arnaud Clement of France who beat Dane Kristian Pless 7-5 6-3.
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The singer was Matt Pless, a former punk rocker from Baltimore who took the bus up to Wall Street.
For Pless, just getting the opportunity to play on the same album as some of the names that later signed on is incredible.
Pless, who is 92nd in the ATP rankings, followed up his victory over defending champion Ivan Ljubicic by beating Escude in just 48 minutes.
Last year, more than 150 bills were introduced in 25 states to regulate energy drilling, said Jacquelyn Pless, an analyst at the National Conference of State Legislatures.
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