Miljan Zekic defeated Valentin Dimov 7-5 7-6 in the Bulgaria F2 round of 32 on clay. Miljan Zekic extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-05-25 | Bulgaria F4 | R16 | clay | Valentin Dimov | 6-2 6-4 |
| 2008-09-01 | Bulgaria F7 | R16 | clay | Miljan Zekic | 7-5 6-3 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.