Fabio Capello is an Italian former football player and manager, famous for his stints at top clubs such as AC Milan, Real Madrid, and Juventus. He is regarded as one of the greatest managers of all time, having won major titles in multiple leagues.
This is based on winning 6 head-to-head matchups with other famous people, but also losing 22 head-to-head matchups.
Most recently Fabio Capello lost a matchup to Madeleine Albright (#1337) voted by someone from United States.