| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2002-05-20 | Dusseldorf | RR | clay | Tim Henman | 6-2 7-6(6) |
| 2000-08-14 | Indianapolis | QF | hard | Tim Henman | 7-6(4) 6-2 |
| 1999-08-09 | Cincinnati Masters | QF | hard | Yevgeny Kafelnikov | 7-5 7-5 |
| 1999-02-15 | Rotterdam | F | hard | Yevgeny Kafelnikov | 6-2 7-6(3) |
| 1998-11-02 | Paris Masters | R16 | hard | Yevgeny Kafelnikov | 6-3 6-7(5) 7-6(2) |
| 1998-09-14 | Tashkent | F | hard | Tim Henman | 7-5 6-4 |
| 1998-02-23 | London | QF | carpet | Yevgeny Kafelnikov | 4-6 6-4 6-2 |
| 1997-11-10 | Tour Finals | RR | hard | Tim Henman | 6-4 6-4 |
| 1997-08-11 | New Haven | QF | hard | Yevgeny Kafelnikov | 5-7 6-3 6-4 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.