| 1. Jornada | 06.08.2023 | FK Bregalnica Štip | - | Sileks Kratovo | 2:1 | ||||
| 2. Jornada | 13.08.2023 | Sileks Kratovo | - | FK Rabotnički | 2:0 | ||||
| 4. Jornada | 23.08.2023 | Vardar Skopje | - | Sileks Kratovo | 2:2 | ||||
| 5. Jornada | 27.08.2023 | Sileks Kratovo | - | Makedonija GP | 2:2 | ||||
| 6. Jornada | 02.09.2023 | KF Gostivari | - | Sileks Kratovo | 1:2 | ||||
| 7. Jornada | 17.09.2023 | Sileks Kratovo | - | KF Shkëndija 79 | 2:1 | ||||
| 8. Jornada | 24.09.2023 | FK AP Brera Strumica | - | Sileks Kratovo | 1:1 | ||||
| 31. Jornada | 04.05.2024 | FK Voska Sport | - | Sileks Kratovo | 2:1 | ||||
| 33. Jornada | 18.05.2024 | FK Bregalnica Štip | - | Sileks Kratovo | 1:1 |  |
Macedonia del Norte