Sergei Krotiouk defeated Evgeny Kirillov 4-6 6-1 6-4 in the Russia F1 round of 32 on hard. The upset overturned the form book — Evgeny Kirillov came in leading the head-to-head 2–0. Sergei Krotiouk claimed a first win over Evgeny Kirillov in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-08-31 | Russia F7 | SF | clay | Evgeny Kirillov | 6-4 5-7 6-2 |
| 2009-08-03 | Russia F3 | R16 | clay | Evgeny Kirillov | 6-1 6-2 |