| 1. Ronde | 06.08.2023 | FC Struga | - | KF Gostivari | 2:0 | ||||
| 2. Ronde | 13.08.2023 | KF Gostivari | - | GFK Tikvesh | 0:3 | ||||
| 3. Ronde | 20.08.2023 | FK Bregalnica Štip | - | KF Gostivari | 2:1 |  |
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| 4. Ronde | 23.08.2023 | KF Gostivari | - | FK Rabotnički | 2:0 | |
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| 5. Ronde | 27.08.2023 | KF Shkupi | - | KF Gostivari | 3:1 | ||||
| 6. Ronde | 02.09.2023 | KF Gostivari | - | Sileks Kratovo | 1:2 | ||||
| 7. Ronde | 17.09.2023 | Makedonija GP | - | KF Gostivari | 3:0 | ||||
| 9. Ronde | 01.10.2023 | KF Gostivari | - | KF Shkëndija 79 | 2:2 |
Noord-Macedonië