Gennaro Gattuso is an Italian football manager and former player, known for his tenacity as a defensive midfielder. He won numerous titles with AC Milan and was a key player in Italy's 2006 World Cup victory.
This is based on winning 5 head-to-head matchups with other famous people, but also losing 19 head-to-head matchups.
Most recently Gennaro Gattuso lost a matchup to Roger Federer (#333) voted by someone from Canada.