| Kup | 08.11.23 | FK Bregalnica Štip | - | FK Voska Sport | 0:1 |  |
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| 1. MFL | 11.11.23 | KF Gostivari | - | FK Bregalnica Štip | 1:0 | ||||
| 1. MFL | 10.12.23 | FC Struga | - | FK Bregalnica Štip | 2:1 | ||||
| 1. MFL | 10.03.24 | GFK Tikvesh | - | FK Bregalnica Štip | 2:1 | ||||
| 1. MFL | 30.10.24 | Sileks Kratovo | - | FK Rabotnički | 1:1 | ||||
| 1. MFL | 24.11.24 | FK Rabotnički | - | KF Besa Dobërdoll | 4:1 | ||||
| 1. MFL | 08.12.24 | FK Rabotnički | - | FK Pelister | 3:0 |
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