Anna Kournikova is clearly the sexiest tennist of all times. One of the most searched terms in Google during her glory days. She never won any significant tournament, although she reached number 8 in the world ranking in 2008. She was, though, a great doubles player, and in she actually reached number 1 in that type of game, winning Grand Slam titles in 1999 and 2002 teaming up with Martina Hingings. Anna is now retired due to back problems. She plays for charity events and has a very active model career.