| 1. Round | 06/08/2023 | FK Bregalnica Štip | - | Sileks Kratovo | 2:1 | ||||
| 2. Round | 13/08/2023 | Sileks Kratovo | - | FK Rabotnički | 2:0 | ||||
| 4. Round | 23/08/2023 | Vardar Skopje | - | Sileks Kratovo | 2:2 | ||||
| 5. Round | 27/08/2023 | Sileks Kratovo | - | Makedonija GP | 2:2 | ||||
| 6. Round | 02/09/2023 | KF Gostivari | - | Sileks Kratovo | 1:2 | ||||
| 7. Round | 17/09/2023 | Sileks Kratovo | - | KF Shkëndija 79 | 2:1 | ||||
| 8. Round | 24/09/2023 | FK AP Brera Strumica | - | Sileks Kratovo | 1:1 | ||||
| 31. Round | 04/05/2024 | FK Voska Sport | - | Sileks Kratovo | 2:1 | ||||
| 33. Round | 18/05/2024 | FK Bregalnica Štip | - | Sileks Kratovo | 1:1 |  |
North Macedonia