| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-03-11 | Indian Wells Masters | SF | hard | Lleyton Hewitt | 6-2 6-4 |
| 2001-08-27 | US Open | F | hard | Lleyton Hewitt | 7-6(4) 6-1 6-1 |
| 2001-06-11 | Queen's Club | SF | grass | Lleyton Hewitt | 3-6 6-3 6-2 |
| 2000-11-27 | Masters Cup | RR | hard | Lleyton Hewitt | 7-5 6-0 |
| 2000-08-28 | US Open | SF | hard | Pete Sampras | 7-6(7) 6-4 7-6(5) |
| 2000-06-12 | Queen's Club | F | grass | Lleyton Hewitt | 6-4 6-4 |
| 2000-03-20 | Miami Masters | SF | hard | Pete Sampras | 6-3 3-6 6-1 |
| 1998-08-17 | New Haven | R32 | hard | Pete Sampras | 6-1 7-6(4) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.