| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-05-02 | Rome Masters | R64 | clay | Tim Henman | 6-3 6-3 |
| 2004-07-26 | Canada Masters | R32 | hard | Gustavo Kuerten | 7-5 6-4 |
| 2002-08-05 | Cincinnati Masters | R64 | hard | Tim Henman | 6-3 6-4 |
| 2001-08-13 | Indianapolis | QF | hard | Gustavo Kuerten | 3-6 6-1 7-5 |
| 2001-08-06 | Cincinnati Masters | SF | hard | Gustavo Kuerten | 6-2 1-6 7-6(4) |
| 2000-08-07 | Cincinnati Masters | SF | hard | Tim Henman | 6-7(11) 6-3 7-6(0) |
| 1998-03-16 | Miami Masters | QF | hard | Tim Henman | 6-2 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.