Daniele De Rossi is an acclaimed Italian football manager and former player, celebrated for his lengthy career with Roma and winning the 2006 FIFA World Cup with Italy. He is currently the head coach of Roma.
This is based on winning 5 head-to-head matchups with other famous people, but also losing 11 head-to-head matchups.
Most recently Daniele De Rossi lost a matchup to Stephen Fry (#270) voted by someone from Canada.