| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-08-30 | US Open | QF | hard | Venus Williams | 7-6(5) 6-4 |
| 2010-05-10 | Madrid | R16 | clay | Venus Williams | 3-6 6-1 6-2 |
| 2010-01-18 | Australian Open | R16 | hard | Venus Williams | 3-6 6-2 6-1 |
| 2008-10-13 | Zurich | QF | hard | Venus Williams | 6-3 6-3 |
| 2004-07-19 | Los Angeles | QF | hard | Venus Williams | 7-5 6-1 |
| 2004-03-24 | Miami | R16 | hard | Venus Williams | 6-1 6-3 |
| 2002-04-30 | Hamburg | R16 | clay | Venus Williams | 6-2 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.