| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2001-08-27 | US Open | R16 | hard | Pete Sampras | 6-3 6-2 6-7(5) 6-4 |
| 2001-03-12 | Indian Wells Masters | QF | hard | Pete Sampras | 4-6 7-6(4) 6-4 |
| 1999-08-09 | Cincinnati Masters | F | hard | Pete Sampras | 7-6(7) 6-3 |
| 1999-05-16 | Dusseldorf | RR | clay | Patrick Rafter | 6-3 6-4 |
| 1998-08-31 | US Open | SF | hard | Patrick Rafter | 6-7(8) 6-4 2-6 6-4 6-3 |
| 1998-08-10 | Cincinnati Masters | F | hard | Patrick Rafter | 1-6 7-6(2) 6-4 |
| 1997-11-10 | Tour Finals | RR | hard | Pete Sampras | 6-4 6-1 |
| 1997-09-23 | Grand Slam Cup | F | carpet | Pete Sampras | 6-2 6-4 7-5 |
| 1997-09-19 | Davis Cup WG SF: USA vs AUS | RR | hard | Pete Sampras | 6-7(6) 6-1 6-1 6-4 |
| 1997-08-04 | Cincinnati Masters | R16 | hard | Pete Sampras | 7-6(4) 6-4 |
| 1997-02-24 | Philadelphia | F | hard | Pete Sampras | 5-7 7-6(4) 6-3 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.