Alessandro Nesta is an Italian football coach and former player, considered one of the greatest defenders of all time. He played for Lazio, AC Milan, and the Italy national team, winning numerous titles including the 2006 FIFA World Cup.
This is based on winning 4 head-to-head matchups with other famous people, but also losing 14 head-to-head matchups.
Most recently Alessandro Nesta lost a matchup to Stellan Skarsgård (#755) voted by someone from Canada.