Valentin Dimov defeated Bogdan Leonte 7-6 6-1 in the Bulgaria F3 round of 16 on clay. The upset overturned the form book — Bogdan Leonte came in leading the head-to-head 1–0, but Valentin Dimov had been the form player, winning 6 of their last 10 on clay. Valentin Dimov claimed a first win over Bogdan Leonte in two meetings, narrowing the head-to-head to 1–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-05-26 | Bulgaria F4 | R32 | clay | Bogdan Leonte | 6-3 6-2 |