| 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 | ||||
| 8. Ronde | 24.09.2023 | Vardar Skopje | - | KF Gostivari | 0:2 | ||||
| 9. Ronde | 01.10.2023 | KF Gostivari | - | KF Shkëndija 79 | 2:2 | ||||
| 10. Ronde | 07.10.2023 | FK AP Brera Strumica | - | KF Gostivari | 0:1 |  |
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| 11. Ronde | 22.10.2023 | KF Gostivari | - | FK Voska Sport | 1:1 | ||||
| 12. Ronde | 29.10.2023 | KF Gostivari | - | FC Struga | 2:1 | ||||
| 13. Ronde | 04.11.2023 | GFK Tikvesh | - | KF Gostivari | 2:2 | |
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| 16. Ronde | 29.11.2023 | KF Gostivari | - | KF Shkupi | 0:0 | ||||
| 17. Ronde | 03.12.2023 | Sileks Kratovo | - | KF Gostivari | 1:1 | ||||
| 21. Ronde | 03.03.2024 | KF Gostivari | - | FK AP Brera Strumica | 2:0 | ||||
| 22. Ronde | 06.03.2024 | FK Voska Sport | - | KF Gostivari | 1:1 |  |
Noord-Macedonië