| 1. Round | 06/08/2023 | GFK Tikvesh | - | Makedonija GP | 1:0 | ||||
| 2. Round | 13/08/2023 | KF Gostivari | - | GFK Tikvesh | 0:3 | ||||
| 3. Round | 20/08/2023 | GFK Tikvesh | - | KF Shkëndija 79 | 1:2 | ||||
| 4. Round | 24/08/2023 | FK AP Brera Strumica | - | GFK Tikvesh | 2:0 | ||||
| 5. Round | 27/08/2023 | GFK Tikvesh | - | FK Voska Sport | 1:1 | ||||
| 11. Round | 22/10/2023 | Sileks Kratovo | - | GFK Tikvesh | 1:0 | ||||
| 14. Round | 11/11/2023 | KF Shkëndija 79 | - | GFK Tikvesh | 1:0 |  |
Germany