Sergei Demekhine defeated Andrei Karatchenia 6-0 6-4 in the Belarus F2 round of 32 on hard. The upset overturned the form book — Andrei Karatchenia came in leading the head-to-head 1–0. Sergei Demekhine claimed a first win over Andrei Karatchenia in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-06-16 | Belarus F2 | R32 | hard | Andrei Karatchenia | 7-6(5) 6-3 |