| 1976 |
Born on March 29 in New York, New York |
| 1981-85 |
Trains with Jimmy Evert |
| 1985-88 |
Trains with Rick Macci |
| 1989 |
Trains with Tom Gullickson |
| 1989 |
Wins six junior singles titles and two junior doubles titles |
| 1990 |
Turns professional |
| 1990 |
Becomes the youngest player ever to reach a professional final |
| 1990 |
Debuts on the Women's Tennis Association rankings at number 25 |
| 1990 |
Youngest ever semifinalist at the French Open |
| 1990 |
Youngest ever seed at Wimbledon |
| 1990 |
Wins first singles title in Puerto Rico |
| 1990 |
Finishes season ranked number eight and becomes youngest ever player to be ranked in the top ten |
| 1991 |
Youngest ever semifinalist at Wimbledon |
| 1991 |
Reaches semifinals at U.S. Open |
| 1991 |
Finishes season ranked number six |
| 1992 |
Reaches three Grand Slam quarterfinals |
| 1992 |
Wins Gold Medal at Olympic Games |
| 1992 |
Becomes the youngest player to surpass the million-dollar mark in career prize money at age 16 |
| 1992 |
Finishes third season ranked number seven |
| 1993 |
Drops off of the Women's Tennis Association tour to finish high school |
| 1993 |
Receives police citation for shoplifting |
| 1994 |
Arrested in Coral Gables, Florida for possession of marijuana |
| 1994 |
Enters drug rehabilitation program in Miami Beach, Florida for 28 days |
| 1994 |
Plays one tournament and loses in the first round |
| 1995 |
Parents divorce |
| 1996 |
Returns to the Women's Tennis Association tour |
| 1996 |
Finishes year ranked number 24 |
| 1997 |
Finishes year ranked number 66 |
| 1998 |
Finishes year ranked number 101 |
| 1999 |
Wins first title in six years in Strasbourg, Germany |
| 1999 |
Finishes season ranked number 23 |
| 2000 |
Reaches first Grand Slam quarterfinal in nine years at the Australian Open |
| 2000 |
Finishes season ranked number 14 |
| 2001 |
Wins first Grand Slam title at the Australian Open |
| 2001 |
Reaches number one ranking for the first time |
| 2001 |
Wins second Grand Slam title at the French Open |
| 2001 |
Ends season with over 50 wins for the first time |
| 2001 |
Finishes season ranked number two |
| 2002 |
Wins third Grand Slam title at the Australian Open |
| 2002 |
Reaches the semifinals at the French Open |
| 2002 |
Reaches the quarterfinals at Wimbledon and the U.S. Open |
| 2002 |
Finishes season ranked number three |
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