| 1. MFL | 22.08.21 | FK Borec | - | FK Bregalnica Štip | 1:1 | ||||
| 1. MFL | 02.10.21 | FK Bregalnica Štip | - | FC Struga | 1:0 | ||||
| 1. MFL | 11.12.21 | GFK Tikvesh | - | FK Bregalnica Štip | 1:3 |  |
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| 1. MFL | 10.04.22 | Makedonija GP | - | FK Bregalnica Štip | 1:1 | |
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| 1. MFL | 14.08.22 | FK Bregalnica Štip | - | FC Struga | 0:1 | ||||
| Kup | 09.11.22 | FC Struga | - | FK Bregalnica Štip | 2:0 | ||||
| 1. MFL | 09.04.23 | FK Bregalnica Štip | - | Makedonija GP | 2:1 | ||||
| 1. MFL | 26.04.23 | KF Shkupi | - | FK Bregalnica Štip | 3:0 |
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