Andrei Karatchenia defeated Sergei Demekhine 7-6 6-3 in the Belarus F2 round of 32 on hard. The upset overturned the form book — Sergei Demekhine came in leading the head-to-head 1–0. Andrei Karatchenia claimed a first win over Sergei Demekhine in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2005-09-12 | Belarus F2 | R32 | hard | Sergei Demekhine | 6-0 6-4 |