Evgeny Donskoy defeated Pavel Chekhov 7-6 6-2 in the Russia F1 round of 32 on carpet. The upset overturned the form book — Pavel Chekhov came in leading the head-to-head 1–0. Evgeny Donskoy claimed a first win over Pavel Chekhov in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-04-14 | Russia F2 | R16 | carpet | Pavel Chekhov | 7-6(5) 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.