Oscar De La Hoya is a retired Mexican-American boxer and current boxing promoter. Known as 'The Golden Boy,' he won 11 world titles in six different weight classes and a gold medal in the 1992 Olympics.
This is based on winning 11 head-to-head matchups with other famous people, but also losing 44 head-to-head matchups.
Most recently Oscar De La Hoya lost a matchup to Sarah Wayne Callies (#1563) voted by someone from United States.