Tennis player whose career was the most disappointing?.

Sabatini - Even though Sabatini challenged Steffi, she usually came up short. However, Sabatini beat Steffi in the 1990 US Open final, for her lone slam title.

Mary Joe Fernandez - Mary Joe was the best player never to win a slam. But Mary Joe had the game to challenge players such as Monica, Sabatini, and Steffi.

Jana Novotna - Outside of Jana capturing Wimbledon in 1998, should have done more. In 1993, Jana let Steffi off the hook in a classic Wimbledon final.

Anna Kournikova- Best player to never win a tournament. Anna is just an updated version of Sabatini

Jennifer Capriati - Jennifer never fulfilled vast potential, and lost too much time because of personal problems.

Conchita Martinez- Just like Sabatini and Jana, should have done more. Conchita beat Martina at 1994 Wimbledon, to capture the Championship.