19. Jennifer Capriati
Achievements as a Teen: Jennifer Capriati debuted at the age of 14 in 1990. Later that season she became the youngest player ever to crack the top 10. Between 1990-1993 (age 14-17) Capriati won six singles titles, including a gold medal at the 1992 Barcelona Olympics.
Career Recap: Capriati finished with a record of 430-176. She tallied 14 career titles and reached number one in the world in 2001. She won the Australian Open back-to-back in 2001-2002, and she took home the French Open title in 2001. Combine those Grand Slam victories with her Olympic gold from 1992, and Caps earned her induction into the Hall of Fame in 2012.