Paolo Maldini is an Italian former professional footballer known as one of the greatest defenders of all time. He played as a left-back and centre-back for AC Milan and the Italy national team, and served as Milan's technical director after retiring.
This is based on winning 5 head-to-head matchups with other famous people, but also losing 15 head-to-head matchups.
Most recently Paolo Maldini lost a matchup to Lil Wayne (#104) voted by someone from Netherlands.