Sergei Demekhine defeated Dmitri Sitak 6-2 6-1 in the St. Petersburg qualifying round on hard. The upset overturned the form book — Dmitri Sitak came in leading the head-to-head 3–0. Sergei Demekhine claimed a first win over Dmitri Sitak in four meetings, narrowing the head-to-head to 3–1.
| 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 |
| 2002-08-19 | Russia F2 | R32 | clay | Dmitri Sitak | 7-5 6-4 |