Ivan Lendl is a Czech-American former professional tennis player, considered one of the greatest of all time. He held the world No. 1 ranking for 270 weeks and won 94 singles titles, including eight major titles.
This is based on winning 1 head-to-head matchups with other famous people, but also losing 25 head-to-head matchups.
Most recently Ivan Lendl lost a matchup to Jeff Buckley (#1205) voted by someone from Brazil.