#3 Jennifer Capriati
The winner of 3 Grand Slam Singles titles, the Olympic Gold at the Barcelona Olympics and former World Number 1 Jennifer Capriati could have possibly gone on to win a lot more titles considering that she rose to stardom while still in her mid-teens.
In 1990, Capriati became the youngest player to reach the semis of the French Open at the tender age of 14. Following her exploits at Roland Garros, she became the youngest ever player to be ranked in the WTA top-10 at 14 years and 235 days.
The 1991 US Open semifinals featured the future of women’s tennis as two teens, Monica Seles and Jennifer Capriati, demonstrated raw aggression and power. Seles, on her way to her third Grand Slam singles crown of the year, won their match in an epic third set tiebreaker. Following her remarkable rise, Capriati battled a lot of personal issues taking a long sabbatical from the Sport. She never regained her form until the turn of the millennium following she re-discovered her mojo to win 3 Grand Slam titles.
Her second semi-final appearance at Flushing Meadows came 10 years after her first in 2001. She would make the semis in New York again in 2003 and 2004 before retiring from the Sport in 2004.