Sergei Krotiouk defeated Ivan Anikanov 6-4 6-3 in the Russia F8 round of 16 on clay. Sergei Krotiouk extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-09-07 | Russia F8 | R16 | hard | Ivan Anikanov | 5-7 6-3 6-1 |
| 2009-08-31 | Russia F7 | QF | clay | Sergei Krotiouk | 6-0 6-4 |