| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-10-02 | Tokyo | F | hard | Roger Federer | 6-3 6-3 |
| 2006-08-28 | US Open | R64 | hard | Roger Federer | 6-3 6-4 7-5 |
| 2006-06-26 | Wimbledon | R64 | grass | Roger Federer | 6-4 6-0 6-2 |
| 2005-03-21 | Miami Masters | QF | hard | Roger Federer | 6-4 6-2 |
| 2004-03-08 | Indian Wells Masters | F | hard | Roger Federer | 6-3 6-3 |
| 2004-02-16 | Rotterdam | QF | hard | Tim Henman | 6-3 7-6(9) |
| 2003-10-27 | Paris Masters | QF | hard | Tim Henman | 7-6(5) 6-1 |
| 2002-03-18 | Miami Masters | R16 | hard | Roger Federer | 6-2 RET |
| 2001-10-22 | Basel | F | hard | Tim Henman | 6-3 6-4 6-2 |
| 2001-06-25 | Wimbledon | QF | grass | Tim Henman | 7-5 7-6(6) 2-6 7-6(6) |
| 2000-10-09 | Vienna | SF | hard | Tim Henman | 2-6 7-6(4) 6-3 |
| 1999-10-04 | Basel | QF | hard | Tim Henman | 6-3 7-5 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.