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| 25.10.2023 | 14:00 | Vardar Skopje | - | Makedonija GP | 0:1 (0:0) | |
| 14:00 | FK Bregalnica Štip | - | Young Team Struga | 11:0 (6:0) | ||
| 14:00 | FK Rabotnički | - | KF Shkëndija 79 | 3:2 (1:2) | ||
| 14:00 | Sileks Kratovo | - | KF Bashkimi | 3:2 (2:0) | ||
| 14:00 | FK Pelister | - | GFK Tikvesh | 0:1 (0:0) | ||
| 14:00 | FK AP Brera Strumica | - | KF Gostivari | 5:4 (0:0) pn. | ||
| 14:00 | KF Shkupi | - | FK Ohrid | 4:0 (1:0) | ||
| 14:00 | FK Voska Sport | - | FC Struga | 4:1 (0:0) pn. |
