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2000s / Federer Upsets Sampras - 2001
The only time two of the greatest and classiest tennis champions of all time--Roger Federer and Pete Sampras--ever met in an ATP match was in the Round of 16 at Wimbledon in 2001. Federer was an unknown 19-year-old Swiss player. He was given virtually zero chance to beat the 30-year-old Sampras who had won Wimbledon seven times and was largely considered to be invincible on grass. Nevertheless Federer evenly battled Sampras through five sets and emerged victorious. This clip shows match point and the aftermath. Check out Federer's goofy hairstyle!