Roger Federer is a retired Swiss tennis player, widely considered one of the greatest in tennis history. He held the world No. 1 ranking for a record 310 weeks, won 20 Grand Slam titles, and amassed 103 ATP titles.
This is based on winning 44 head-to-head matchups with other famous people, but also losing 47 head-to-head matchups.
Most recently Roger Federer lost a matchup to Elton John (#149) voted by someone from United States.