Damian Lillard is an American professional basketball player for the Milwaukee Bucks in the NBA, known for his clutch performances and nicknamed 'Dame Time'. He has been a multiple-time NBA All-Star and won the NBA Rookie of the Year in 2013.
This is based on winning 7 head-to-head matchups with other famous people, but also losing 70 head-to-head matchups.
Most recently Damian Lillard lost a matchup to Steve-O (#1061) voted by someone from Canada.