Darko Madjarovski defeated Yordan Kanev 6-1 3-6 6-2 in the Serbia & Montenegro F3 qualifying round on clay. The result followed the form book — Darko Madjarovski came in leading the head-to-head 2–0. Darko Madjarovski extended the head-to-head to 3–0.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2006-08-07 | Serbia & Montenegro F4 | R32 | clay | Darko Madjarovski | 7-6(5) 6-2 |
| 2001-04-23 | Bulgaria 3 | R32 | clay | Darko Madjarovski | 6-4 7-5 |