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 10 head-to-head matchups.
Most recently Daniele De Rossi lost a matchup to Drake (#169) voted by someone from United States.