Pete Sampras is a former world No. 1 American tennis player known for his powerful serve and precise gameplay. He won 14 major singles titles, including seven Wimbledon titles, two Australian Opens, and five US Opens. Sampras was inducted into the International Tennis Hall of Fame in 2007.
This is based on winning 4 head-to-head matchups with other famous people, but also losing 12 head-to-head matchups.
Most recently Pete Sampras lost a matchup to Cynthia Nixon (#263) voted by someone from Canada.