| Kup | 09.11.22 | FC Struga | - | FK Bregalnica Štip | 2:0 | ||||
| 1. MFL | 09.04.23 | FK Bregalnica Štip | - | Makedonija GP | 2:1 |  |
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| 1. MFL | 26.04.23 | KF Shkupi | - | FK Bregalnica Štip | 3:0 | ||||
| 1. MFL | 13.08.23 | Makedonija GP | - | FK Bregalnica Štip | 1:0 | ||||
| 1. MFL | 02.09.23 | FK Voska Sport | - | FK Bregalnica Štip | 2:0 | ||||
| 1. MFL | 17.09.23 | FK Bregalnica Štip | - | FC Struga | 1:3 |  |
Ouganda