Martina Hingis is a Swiss former professional tennis player known for being the first Swiss player to win a major title and attain the world No. 1 ranking. She won five major singles titles and 20 total Grand Slam titles.
This is based on winning 11 head-to-head matchups with other famous people, but also losing 14 head-to-head matchups.
Most recently Martina Hingis lost a matchup to Ken Watanabe (#865) voted by someone from Canada.