| Kup | 08.11.23 | FK Bregalnica Štip | - | FK Voska Sport | 0:1 | ||||
| 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 | 16.03.24 | Sileks Kratovo | - | FK AP Brera Strumica | 2:1 | ||||
| 1. MFL | 21.04.24 | KF Gostivari | - | FK AP Brera Strumica | 1:1 | ||||
| 1. MFL | 28.04.24 | FK AP Brera Strumica | - | Vardar Skopje | 2:0 |  |
Macedonia del Norte