| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2003-10-20 | St. Petersburg | R32 | carpet | Yevgeny Kafelnikov | 2-6 6-3 6-4 |
| 2003-07-21 | Indianapolis | R16 | hard | Nicolas Kiefer | 6-3 6-4 |
| 2002-09-30 | Moscow | R16 | hard | Yevgeny Kafelnikov | 6-4 6-2 |
| 2002-06-10 | Halle | F | grass | Yevgeny Kafelnikov | 2-6 6-4 6-4 |
| 2002-04-29 | Munich | R32 | clay | Nicolas Kiefer | 6-4 6-7(7) 6-3 |
| 2001-10-01 | Moscow | F | hard | Yevgeny Kafelnikov | 6-4 7-5 |
| 2001-02-19 | Rotterdam | R16 | hard | Nicolas Kiefer | 6-4 6-2 |
| 1999-11-22 | Tour Finals | RR | hard | Nicolas Kiefer | 6-1 4-6 6-2 |
| 1999-10-11 | Vienna | QF | hard | Nicolas Kiefer | 6-0 6-4 |
| 1999-08-16 | Washington | SF | hard | Yevgeny Kafelnikov | 6-2 2-6 6-3 |
| 1999-04-02 | Davis Cup WG R1: GER vs RUS | RR | carpet | Yevgeny Kafelnikov | 7-6(5) 6-4 6-4 |
| 1998-08-31 | US Open | R32 | hard | Yevgeny Kafelnikov | 6-4 6-0 6-2 |
| 1997-06-23 | Wimbledon | R16 | grass | Nicolas Kiefer | 6-2 7-5 2-6 6-1 |
| 1997-06-09 | Halle | R16 | grass | Yevgeny Kafelnikov | 7-6(3) 7-6(2) |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.