Wayne Gretzky is a retired Canadian ice hockey player and coach widely considered the greatest hockey player of all time. He holds numerous records, including most career goals and assists in NHL history.
This is based on winning 16 head-to-head matchups with other famous people, but also losing 16 head-to-head matchups.
Most recently Wayne Gretzky lost a matchup to Sally Field (#1833) voted by someone from United States.