| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-05-29 | Roland Garros | R128 | clay | Mark Philippoussis | 4-6 7-5 7-6(4) 4-6 8-6 |
| 1999-02-08 | San Jose | SF | hard | Mark Philippoussis | W/O |
| 1998-11-02 | Paris Masters | QF | hard | Pete Sampras | 6-3 6-3 |
| 1998-06-22 | Wimbledon | QF | grass | Pete Sampras | 7-6(5) 6-4 6-4 |
| 1997-09-19 | Davis Cup WG SF: USA vs AUS | RR | hard | Pete Sampras | 6-1 6-2 7-6(5) |
| 1997-05-19 | Dusseldorf | RR | clay | Mark Philippoussis | 4-6 6-4 0-1 RET |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.