| 1. Ronde | 06.08.2023 | FC Struga | - | KF Gostivari | 2:0 |  |
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| 2. Ronde | 13.08.2023 | KF Gostivari | - | GFK Tikvesh | 0:3 | ||||
| 3. Ronde | 20.08.2023 | FK Bregalnica Štip | - | KF Gostivari | 2:1 | ||||
| 4. Ronde | 23.08.2023 | KF Gostivari | - | FK Rabotnički | 2:0 | ||||
| 5. Ronde | 27.08.2023 | KF Shkupi | - | KF Gostivari | 3:1 | ||||
| 6. Ronde | 02.09.2023 | KF Gostivari | - | Sileks Kratovo | 1:2 | ||||
| 10. Ronde | 07.10.2023 | FK AP Brera Strumica | - | KF Gostivari | 0:1 | ||||
| 11. Ronde | 22.10.2023 | KF Gostivari | - | FK Voska Sport | 1:1 |
Noord-Macedonië