Sergei Yaroshenko defeated Evgueni Smirnov 6-3 6-2 in the Russia F1 round of 32 on clay. The result followed the form book — Sergei Yaroshenko came in leading the head-to-head 1–0. Sergei Yaroshenko extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 1999-08-23 | Ukraine F4 | R32 | clay | Sergei Yaroshenko | 6-1 6-3 |