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| 08.11.2023 | 13:00 | GFK Tikvesh | - | FK AP Brera Strumica | 6:5 (0:1, 1:1) i.E. | |
| 13:00 | FK Bregalnica Štip | - | FK Voska Sport | 0:1 (0:0) | ||
| 13:00 | Makedonija GP | - | Sileks Kratovo | 1:0 (0:0) | ||
| 09.11.2023 | 13:00 | FK Rabotnički | - | KF Shkupi | 0:1 (0:1) |
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| 08.11.2023 | 13:00 | GFK Tikvesh | - | FK AP Brera Strumica | 6:5 (0:1, 1:1) i.E. | |
| 13:00 | FK Bregalnica Štip | - | FK Voska Sport | 0:1 (0:0) | ||
| 13:00 | Makedonija GP | - | Sileks Kratovo | 1:0 (0:0) | ||
| 09.11.2023 | 13:00 | FK Rabotnički | - | KF Shkupi | 0:1 (0:1) |
