| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-08-26 | US Open | F | hard | Pete Sampras | 6-3 6-4 5-7 6-4 |
| 2002-04-22 | Houston | SF | clay | Pete Sampras | 6-1 7-5 |
| 2001-07-23 | Los Angeles | F | hard | Andre Agassi | 6-4 6-2 |
| 2001-03-12 | Indian Wells Masters | F | hard | Andre Agassi | 7-6(5) 7-5 6-1 |
| 2000-01-17 | Australian Open | SF | hard | Andre Agassi | 6-4 3-6 6-7(0) 7-6(5) 6-1 |
| 1999-11-22 | Tour Finals | F | hard | Pete Sampras | 6-1 7-5 6-4 |
| 1999-11-22 | Tour Finals | RR | hard | Andre Agassi | 6-2 6-2 |
| 1999-08-09 | Cincinnati Masters | SF | hard | Pete Sampras | 7-6(7) 6-4 |
| 1999-07-26 | Los Angeles | F | hard | Pete Sampras | 7-6(3) 7-6(1) |
| 1999-06-21 | Wimbledon | F | grass | Pete Sampras | 6-3 6-4 7-5 |
| 1998-08-03 | Canada Masters | QF | hard | Andre Agassi | 6-7(5) 6-1 6-2 |
| 1998-04-20 | Monte Carlo Masters | R32 | clay | Pete Sampras | 6-4 7-5 |
| 1998-02-09 | San Jose | F | hard | Andre Agassi | 6-2 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.