Landon Donovan is an American former professional soccer player, widely considered one of the greatest American players of all time. He holds records for most international assists, tied for most international goals scored by an American player, and has won a record six MLS Cups.
This is based on winning 4 head-to-head matchups with other famous people, but also losing 18 head-to-head matchups.
Most recently Landon Donovan lost a matchup to Jean-Michel Basquiat (#1394) voted by someone from United Kingdom.