Dmitri Sitak defeated Denis Matsukevitch 6-2 6-1 in the Moscow q16 on hard. The upset overturned the form book — Denis Matsukevitch came in leading the head-to-head 3–1. Dmitri Sitak narrowed the head-to-head to 3–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-04-13 | Russia F2 | R16 | carpet | Denis Matsukevitch | 6-3 6-3 |
| 2007-05-14 | Uzbekistan F2 | R16 | hard | Dmitri Sitak | 7-6(9) 6-3 |
| 2005-06-13 | Spain F12 | R16 | hard | Denis Matsukevitch | 6-2 6-4 |
| 2005-05-02 | Uzbekistan F3 | QF | hard | Denis Matsukevitch | 6-1 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.