| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-05-24 | Roland Garros | R128 | clay | Venus Williams | 6-3 6-3 |
| 2010-05-03 | Rome | R32 | clay | Venus Williams | 6-2 6-2 |
| 2006-05-29 | Roland Garros | R16 | clay | Venus Williams | 4-6 6-3 6-2 |
| 2006-05-15 | Rome | R16 | clay | Venus Williams | 7-6(2) 3-6 6-1 |
| 2005-07-25 | Stanford | SF | hard | Venus Williams | 2-6 7-6(4) 6-2 |
| 2002-11-06 | WTA Tour Championships | R16 | carpet | Venus Williams | 6-2 7-6(7) |
| 2001-12-30 | Gold Coast | R16 | hard | Venus Williams | 6-0 6-4 |
| 2000-08-21 | New Haven | QF | hard | Venus Williams | 6-4 6-2 |
| 1998-09-28 | Grand Slam Cup | F | hard | Venus Williams | 6-2 3-6 6-2 |
| 1998-01-19 | Australian Open | R16 | hard | Venus Williams | 6-4 6-1 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.