| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-06-20 | Wimbledon | F | grass | Venus Williams | 4-6 7-6(4) 9-7 |
| 2005-04-04 | Amelia Island | QF | clay | Lindsay Davenport | 1-6 6-3 6-4 |
| 2004-07-19 | Los Angeles | SF | hard | Lindsay Davenport | 7-5 2-0 RET |
| 2004-07-12 | Stanford | F | hard | Lindsay Davenport | 7-6(4) 5-7 7-6(4) |
| 2003-06-23 | Wimbledon | QF | grass | Venus Williams | 6-2 2-6 6-1 |
| 2002-08-19 | New Haven | F | hard | Venus Williams | 7-5 6-0 |
| 2002-07-29 | San Diego | SF | hard | Venus Williams | 6-2 6-1 |
| 2001-08-19 | New Haven | F | hard | Venus Williams | 7-6(6) 6-4 |
| 2001-07-30 | San Diego | SF | hard | Venus Williams | 6-2 7-5 |
| 2001-06-25 | Wimbledon | SF | grass | Venus Williams | 6-2 6-7(1) 6-1 |
| 2000-10-14 | Linz | F | hard | Lindsay Davenport | 6-4 3-6 6-2 |
| 2000-08-22 | US Open | F | hard | Venus Williams | 6-4 7-5 |
| 2000-07-24 | Stanford | F | hard | Venus Williams | 6-1 6-4 |
| 2000-06-26 | Wimbledon | F | grass | Venus Williams | 6-3 7-6 |
| 1999-11-08 | Philadelphia | SF | carpet | Lindsay Davenport | 6-1 6-2 |
| 1999-08-23 | New Haven | F | hard | Venus Williams | 6-2 7-5 |
| 1999-08-02 | San Diego | SF | hard | Venus Williams | 6-4 7-5 |
| 1999-07-26 | Stanford | F | hard | Lindsay Davenport | 7-6 6-2 |
| 1999-01-18 | Australian Open | QF | hard | Lindsay Davenport | 6-4 6-0 |
| 1998-10-12 | Zurich | F | hard | Lindsay Davenport | 7-5 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.