Pavel Chekhov defeated Evgeny Donskoy 7-6 6-4 in the Russia F2 round of 16 on carpet. The upset overturned the form book — Evgeny Donskoy came in leading the head-to-head 1–0. Pavel Chekhov claimed a first win over Evgeny Donskoy in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-04-06 | Russia F1 | R32 | carpet | Evgeny Donskoy | 7-6(8) 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.