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Anna Wintour looked quite the chic cheerleader last night. Poised next to Rupert Murdoch, she watched her favorite Fashion Week buddy, Roger Federer, battle it out against tennis hero Pete Sampras at the sold-out Madison Square Garden. In fact, an assortment of celebrities —Tiger Woods, Chloë Sevigny, Regis Philbin, and a fresh-from-court Barry Diller —showed up to watch the dashing Federer and the legendary Sampras fight it out on the court. But while the two tennis greats were fierce during the game, they were friendly before, during a Q&A session in front of a VIP crowd in the NetJets private lounge, where they compared Wimbledon wins, private-plane experiences, “favorite strokes” (they both like their serves), and training schedules. Federer says he plays for four to five hours a day, in addition to body conditioning and routine massages. “Yeah, it’s pretty much the same for me,” the now-retired Sampras agreed, then paused and said he was kidding. “To be honest, I get bored after about an hour.” When asked if he had any advice for the reigning champ Federer, Sampras smiled: “Sure. Quit now.” Then Federer beat him. —Katie Goldsmith
