| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-04-22 | Houston | QF | clay | Pete Sampras | 6-2 7-6(3) |
| 2001-12-31 | Adelaide | R32 | hard | Todd Martin | 3-6 6-3 6-4 |
| 2001-01-15 | Australian Open | R16 | hard | Todd Martin | 6-7(2) 6-3 6-4 6-4 |
| 1998-11-02 | Paris Masters | SF | hard | Pete Sampras | 6-4 7-6(5) |
| 1998-10-19 | Lyon | R32 | clay | Pete Sampras | 6-4 1-6 6-4 |
| 1998-10-12 | Vienna | SF | hard | Pete Sampras | 6-3 7-6(4) |
| 1998-03-09 | Indian Wells Masters | R32 | hard | Pete Sampras | 6-1 7-5 |
| 1997-02-10 | San Jose | SF | hard | Pete Sampras | 6-2 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.