| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-07-22 | Los Angeles | QF | hard | Andre Agassi | 7-6(3) 3-6 6-4 |
| 2001-07-23 | Los Angeles | SF | hard | Andre Agassi | 6-7(3) 6-3 6-3 |
| 2000-11-27 | Masters Cup | RR | hard | Andre Agassi | 4-6 6-4 6-3 |
| 2000-11-27 | Masters Cup | F | hard | Gustavo Kuerten | 6-4 6-4 6-4 |
| 2000-03-20 | Miami Masters | SF | hard | Gustavo Kuerten | 6-1 6-4 |
| 1999-11-22 | Tour Finals | RR | hard | Andre Agassi | 6-4 7-5 |
| 1999-08-09 | Cincinnati Masters | QF | hard | Andre Agassi | 6-2 7-6(10) |
| 1999-06-21 | Wimbledon | QF | grass | Andre Agassi | 6-3 6-4 6-4 |
| 1998-02-09 | San Jose | R16 | hard | Andre Agassi | 6-3 6-1 |
| 1997-08-04 | Cincinnati Masters | R64 | hard | Gustavo Kuerten | 6-3 6-1 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.