| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-12-30 | Gold Coast | QF | hard | Venus Williams | 6-2 6-4 |
| 2000-10-14 | Linz | R16 | hard | Venus Williams | 7-5 6-2 |
| 2000-06-26 | Wimbledon | R64 | grass | Venus Williams | 6-1 6-4 |
| 1998-05-25 | Roland Garros | R64 | clay | Venus Williams | 6-0 6-2 |
| 1998-01-11 | Sydney | SF | hard | Venus Williams | 6-1 7-6 |
| 1997-03-07 | Indian Wells | R32 | hard | Venus Williams | 3-6 6-3 6-2 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.