Miljan Zekic defeated Vladimir Obradovic 7-6 6-4 in the Serbia F5 qualifying round on clay. The upset overturned the form book — Vladimir Obradovic came in leading the head-to-head 4–1. Miljan Zekic narrowed the head-to-head to 4–2.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2013-08-26 | Serbia F11 | R32 | clay | Miljan Zekic | 7-6(4) 6-4 |
| 2010-06-28 | Serbia F3 | QF | clay | Vladimir Obradovic | 5-7 6-1 6-4 |
| 2009-07-25 | Umag | Q32 | clay | Vladimir Obradovic | 6-4 7-6(6) |
| 2007-08-06 | Serbia F3 | R16 | clay | Vladimir Obradovic | 2-6 6-2 6-4 |
| 2006-08-07 | Serbia & Montenegro F4 | R32 | clay | Vladimir Obradovic | 6-0 6-4 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.