Lothar Matthäus is a renowned German football pundit and former player and manager. He captained West Germany to victory in the 1990 FIFA World Cup and was awarded the Ballon d'Or the same year. He is celebrated for his versatility and tactical acumen on the field.
This is based on winning 5 head-to-head matchups with other famous people, but also losing 12 head-to-head matchups.
Most recently Lothar Matthäus lost a matchup to Anna Kournikova (#1297) voted by someone from United States.