Dusan Obradovic defeated J. Kupcic 7-5 2-6 7-5 in the M15 Brcko 1 round of 16 on clay. Dusan Obradovic extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2025-05-28 | M15 Doboj 1 | R32 | clay | J. Kupcic | 7-6(5) 6-4 |
| 2024-05-01 | M15 Osijek 1 | R32 | clay | Dusan Obradovic | 6-3 6-2 |
Averages over each player's completed matches in the selected window. ATP, WTA & Challenger.