Jimmy Hill was an English footballer and television personality. He influenced football in numerous ways, including abolishing the maximum wage, introducing goal difference, and broadcasting innovations. He also managed Coventry City and presented BBC’s Match of the Day.
This is based on winning 8 head-to-head matchups with other famous people, but also losing 61 head-to-head matchups.
Most recently Jimmy Hill lost a matchup to Katie Couric (#1606) voted by someone from United States.