Yevgeny Kafelnikov defeated Wayne Black 6-4 4-6 6-4 in the New Haven round of 16 on hard. The result followed the form book — Yevgeny Kafelnikov came in leading the head-to-head 1–0, defending last year's round of 64. Yevgeny Kafelnikov extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-16 | Washington | R32 | hard | Yevgeny Kafelnikov | 0-6 6-2 6-4 |
Averages over each player's completed matches in the selected window (200 vs 111). 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