Darko Madjarovski defeated Todor Enev 6-3 6-4 in the Bulgaria F2 round of 16 on clay. The result followed the form book — Darko Madjarovski came in leading the head-to-head 1–0. Darko Madjarovski extended the head-to-head to 2–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-08-14 | Serbia & Montenegro F5 | R16 | clay | Darko Madjarovski | 6-4 6-0 |