Artem Smirnov defeated Vladyslav Klymenko 6-2 6-4 in the Germany F9 qualifying round on clay. Artem Smirnov extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-08-18 | Russia F4 | R32 | clay | Vladyslav Klymenko | 6-3 4-6 6-1 |
| 2007-06-04 | Ukraine F2 | R32 | clay | Artem Smirnov | 7-5 7-6(4) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.