Bradley Wiggins is a British former professional cyclist who transitioned from track to road racing. He is the first to win both World and Olympic championships on track and road, and the Tour de France. He held the Guinness World Records he set, and his accolades include multiple Olympic golds and world titles.
This is based on winning 3 head-to-head matchups with other famous people, but also losing 22 head-to-head matchups.
Most recently Bradley Wiggins lost a matchup to Cybill Shepherd (#1429) voted by someone from United States.