| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-08-27 | US Open | R16 | hard | Venus Williams | 6-4 6-0 |
| 2001-08-19 | New Haven | R16 | hard | Venus Williams | 7-6(5) 6-3 |
| 1999-11-08 | Philadelphia | QF | carpet | Venus Williams | 6-1 7-6 |
| 1999-08-02 | San Diego | QF | hard | Venus Williams | 7-5 6-1 |
| 1997-08-25 | US Open | QF | hard | Venus Williams | 7-5 7-5 |
Averages from each player's recent completed matches (1 vs 20). ATP, WTA & Challenger.