Ray Allen is an American former professional basketball player, renowned for his exceptional three-point shooting. Holding an 18-year career in the NBA, Allen won two NBA championships and was inducted into the Naismith Memorial Basketball Hall of Fame.
This is based on winning 3 head-to-head matchups with other famous people, but also losing 16 head-to-head matchups.
Most recently Ray Allen lost a matchup to Sid Vicious (#1966) voted by someone from Canada.