| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2004-02-09 | San Jose | QF | hard | Andre Agassi | 7-6(4) 7-5 |
| 2002-10-14 | Madrid Masters | R32 | clay | Andre Agassi | 6-4 6-4 |
| 2002-08-26 | US Open | R16 | hard | Andre Agassi | 6-2 6-3 6-3 |
| 2002-07-22 | Los Angeles | F | hard | Andre Agassi | 6-2 6-4 |
| 2001-07-23 | Los Angeles | QF | hard | Andre Agassi | 6-2 7-5 |
| 2001-03-19 | Miami Masters | F | hard | Andre Agassi | 7-6(4) 6-1 6-0 |
| 2001-02-26 | San Jose | SF | hard | Andre Agassi | 6-4 6-4 |
| 1999-03-01 | Scottsdale | SF | hard | Jan Michael Gambill | 5-4 RET |
| 1998-07-27 | Los Angeles | R16 | hard | Andre Agassi | 6-4 6-4 |
| 1998-03-09 | Indian Wells Masters | QF | hard | Jan Michael Gambill | 7-6(6) 3-6 6-3 |
| 1998-03-02 | Scottsdale | QF | hard | Andre Agassi | 6-3 7-6(5) |
| 1998-02-09 | San Jose | QF | hard | Andre Agassi | 7-5 7-6(7) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.