Vladimir Obradovic advanced when Dejan Katic retired 6-3 3-0 in the Serbia F7 qualifying round. Vladimir Obradovic extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2010-06-14 | Serbia F1 | R16 | clay | Vladimir Obradovic | 6-4 7-6(1) |
| 2006-08-07 | Serbia & Montenegro F4 | R16 | clay | Dejan Katic | 6-7(2) 6-4 7-5 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.