Yevgeny Kafelnikov defeated Mark Philippoussis 7-6 6-4 in the Paris Masters round of 32 on hard. Yevgeny Kafelnikov extended the head-to-head to 4–3.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2000-11-13 | Paris Masters | R16 | hard | Mark Philippoussis | 6-4 6-2 |
| 2000-09-18 | Sydney Olympics | R16 | hard | Yevgeny Kafelnikov | 7-6(4) 6-3 |
| 1998-10-26 | Stuttgart Masters | R32 | carpet | Yevgeny Kafelnikov | 4-6 6-4 7-6(4) |
| 1998-06-22 | Wimbledon | R128 | grass | Mark Philippoussis | 6-7(5) 7-6(1) 6-4 6-2 |
| 1997-09-29 | Basel | QF | hard | Mark Philippoussis | 6-3 6-7(5) 6-2 |
| 1997-05-26 | Roland Garros | R16 | clay | Yevgeny Kafelnikov | 6-2 6-3 7-5 |
Averages from each player's recent completed matches (20 vs 20). ATP, WTA & Challenger.