| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-07-31 | Washington | R16 | hard | Tim Henman | 6-1 6-3 |
| 2003-05-12 | Hamburg Masters | R64 | clay | Tim Henman | 7-5 6-4 |
| 2003-03-10 | Indian Wells Masters | R64 | hard | Tim Henman | 7-5 6-2 |
| 2001-08-06 | Cincinnati Masters | QF | hard | Tim Henman | 4-6 6-2 6-2 |
| 1999-11-08 | Stockholm | R16 | hard | Jan Michael Gambill | 7-5 6-3 |
| 1998-10-26 | Stuttgart Masters | R16 | carpet | Jan Michael Gambill | 7-6(2) 1-6 7-6(5) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.