Dmitri Sitak defeated Sergei Demekhine 7-5 6-4 in the Russia F2 round of 32 on clay. The result followed the form book — Dmitri Sitak came in leading the head-to-head 2–0. Dmitri Sitak extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-04-07 | Russia F1 | R32 | carpet | Dmitri Sitak | 6-4 6-3 |
| 2006-10-07 | Moscow | Q32 | hard | Dmitri Sitak | 6-3 4-6 6-4 |