Vladimir Obradovic defeated Darko Madjarovski 7-6 7-6 in the Serbia F4 qualifying round on clay. The upset overturned the form book — Darko Madjarovski came in leading the head-to-head 4–0. Vladimir Obradovic claimed a first win over Darko Madjarovski in five meetings, narrowing the head-to-head to 4–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2009-06-15 | Serbia F3 | R32 | clay | Darko Madjarovski | 6-3 6-2 |
| 2006-06-26 | Serbia & Montenegro F2 | QF | clay | Darko Madjarovski | 3-6 7-6(5) 7-6(6) |
| 2003-06-16 | Serbia & Montenegro F2 | R32 | clay | Darko Madjarovski | 7-6(5) 7-6(3) |
| 2002-06-03 | Slovenia F1 | R32 | clay | Darko Madjarovski | 4-6 6-3 7-6(8) |