Ruud van Nistelrooy is a Dutch football coach and former player, renowned as one of the best strikers of his era. He was the top scorer in three UEFA Champions League seasons and enjoyed successful stints with Manchester United and Real Madrid.
This is based on winning 6 head-to-head matchups with other famous people, but also losing 19 head-to-head matchups.
Most recently Ruud van Nistelrooy lost a matchup to Josh Hartnett (#1492) voted by someone from United States.