Ana Ivanovic is a retired Serbian tennis player and former world No. 1. She won the 2008 French Open and held the top ranking for 12 weeks. With 15 WTA titles, she is known for her aggressive play style.
This is based on winning 10 head-to-head matchups with other famous people, but also losing 14 head-to-head matchups.
Most recently Ana Ivanovic lost a matchup to Kris Kristofferson (#1730) voted by someone from United States.