| 1. Jornada | 06.08.2023 | FK Bregalnica Štip | - | Sileks Kratovo | 2:1 |  |
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| 2. Jornada | 13.08.2023 | Sileks Kratovo | - | FK Rabotnički | 2:0 | ||||
| 3. Jornada | 20.08.2023 | KF Shkupi | - | Sileks Kratovo | 1:1 | ||||
| 4. Jornada | 23.08.2023 | Vardar Skopje | - | Sileks Kratovo | 2:2 |  |
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| 7. Jornada | 17.09.2023 | Sileks Kratovo | - | KF Shkëndija 79 | 2:1 | ||||
| 10. Jornada | 08.10.2023 | FC Struga | - | Sileks Kratovo | 2:0 | ||||
| 11. Jornada | 22.10.2023 | Sileks Kratovo | - | GFK Tikvesh | 1:0 |
Macedonia del Norte