| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-02-03 | Tokyo | QF | hard | Chanda Rubin | W/O |
| 2002-08-26 | US Open | R16 | hard | Venus Williams | 6-2 4-6 7-5 |
| 2002-05-27 | Roland Garros | R16 | clay | Venus Williams | 6-3 6-2 |
| 2000-10-14 | Linz | SF | hard | Venus Williams | 6-4 6-0 |
| 2000-05-15 | Rome | R32 | clay | Venus Williams | 6-1 6-2 |
| 1999-01-18 | Australian Open | R16 | hard | Venus Williams | 7-6(3) 6-4 |
| 1998-08-03 | San Diego | R16 | hard | Venus Williams | 6-3 6-2 |
| 1998-06-22 | Wimbledon | R32 | grass | Venus Williams | 6-3 6-4 |
| 1997-06-17 | Eastbourne | R32 | grass | Venus Williams | 6-4 6-4 |
| 1997-04-07 | Amelia Island | R32 | clay | Chanda Rubin | 6-4 6-0 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.