| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-15 | WTA Tour Championships | QF | carpet | Venus Williams | 6-4 7-6 |
| 1999-09-27 | Grand Slam Cup | QF | hard | Venus Williams | 6-3 6-4 |
| 1999-08-30 | US Open | QF | hard | Venus Williams | 6-4 6-3 |
| 1998-06-22 | Wimbledon | R64 | grass | Venus Williams | 6-1 6-2 |
Averages from each player's recent completed matches (14 vs 20). ATP, WTA & Challenger.