Dennis Dragomirov defeated J. Kupcic 6-4 7-6 in the M15 Kottingbrunn 1 q64 on clay. Dennis Dragomirov extended the head-to-head to 2–1.
| Date | Tournament | Round | Surface | Winner | Score |
|---|---|---|---|---|---|
| 2024-06-03 | M15 Hrastnik 1 | Q32 | clay | J. Kupcic | 6-1 6-3 |
| 2022-08-15 | M15 Bad Waltersdorf 1 | Q32 | clay | Dennis Dragomirov | 6-3 6-4 |