Yevgeny Kafelnikov defeated Byron Black 7-6 6-2 in the Moscow quarter-final on hard. The result followed the form book — Yevgeny Kafelnikov came in leading the head-to-head 6–0, defending last year's semi-final. Yevgeny Kafelnikov extended the head-to-head to 7–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-11-08 | Moscow | F | hard | Yevgeny Kafelnikov | 7-6 6-4 |
| 1999-02-22 | London | R16 | carpet | Yevgeny Kafelnikov | 6-3 6-2 |
| 1997-11-03 | Moscow | R16 | hard | Yevgeny Kafelnikov | 6-4 6-3 |
| 1996-06-17 | Halle | R16 | grass | Yevgeny Kafelnikov | 6-3 6-4 |
| 1996-01-01 | Adelaide | F | hard | Yevgeny Kafelnikov | 7-6 3-6 6-1 |
| 1995-11-06 | Moscow | QF | hard | Yevgeny Kafelnikov | 6-7(2) 6-0 6-0 |
Averages over each player's completed matches in the selected window (200 vs 200). ATP, WTA & Challenger.
Each player's serve crossed against the other's return, converted to expected hold of serve. Recent completed matches, ATP, WTA & Challenger. About