Nikola Ciric defeated Darko Madjarovski 6-4 6-4 in the Serbia F1 qualifying round on clay. Nikola Ciric extended the head-to-head to 5–4.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2008-09-29 | Bosnia & Herzegovina F7 | R32 | clay | Darko Madjarovski | 6-1 6-1 |
| 2006-09-04 | Bulgaria F3 | QF | clay | Nikola Ciric | 6-4 3-6 6-3 |
| 2006-08-14 | Serbia & Montenegro F5 | F | clay | Nikola Ciric | 6-7(4) 6-1 6-3 |
| 2006-07-31 | Serbia & Montenegro F3 | SF | clay | Darko Madjarovski | 6-3 4-0 |
| 2006-06-19 | Serbia & Montenegro F1 | R32 | clay | Nikola Ciric | 6-4 7-5 |
| 2005-09-05 | Belarus F1 | R16 | clay | Darko Madjarovski | 7-5 6-0 |
| 2005-04-25 | Hungary F1 | R16 | clay | Nikola Ciric | 6-1 4-6 7-6(6) |
| 2001-08-13 | Yugoslavia 3 | R16 | clay | Darko Madjarovski | 6-2 7-6(7) |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.