Vladzimir Kruk defeated Ivan Anikanov 6-7 6-3 7-6 in the Kazakhstan F8 round of 16 on hard. The upset overturned the form book — Ivan Anikanov came in leading the head-to-head 1–0. Vladzimir Kruk claimed a first win over Ivan Anikanov in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-08-31 | Russia F7 | R16 | clay | Ivan Anikanov | 6-2 6-1 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.