Martina Navratilova is a former Czech-American tennis player, widely considered one of the greatest in the sport's history. She won a total of 59 major titles and held the world No. 1 ranking in singles for 332 weeks.
This is based on winning 3 head-to-head matchups with other famous people, but also losing 18 head-to-head matchups.
Most recently Martina Navratilova lost a matchup to Ron Perlman (#759) voted by someone from United Kingdom.