Sergei Demekhine defeated Ilya Belyaev 6-4 6-3 in the Romania F3 round of 32 on clay. The upset overturned the form book — Ilya Belyaev came in leading the head-to-head 2–0. Sergei Demekhine claimed a first win over Ilya Belyaev in three meetings, narrowing the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-10-04 | Moscow | Q32 | hard | Ilya Belyaev | 6-1 5-7 6-4 |
| 2008-09-15 | Russia F8 | QF | clay | Ilya Belyaev | 6-3 6-0 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.