Gary Neville is a former English right-back who spent his entire career at Manchester United, winning multiple Premier League and UEFA Champions League titles. He later became a football pundit and worked as an assistant manager and head coach.
This is based on winning 4 head-to-head matchups with other famous people, but also losing 20 head-to-head matchups.
Most recently Gary Neville lost a matchup to Andy Serkis (#1149) voted by someone from United States.