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| 20.09.2023 | 15:00 | Young Team Struga | - | FK Pobeda Junior | 4:3 (0:0) pn. | |
| 15:00 | FK Novaci 2005 | - | FK Bregalnica Štip | 0:8 (0:4) | ||
| 15:00 | KF Bashkimi | - | FK Skopje | 4:3 (0:1) pn. | ||
| 15:00 | KF Arsimi | - | GFK Tikvesh | 1:2 (0:2) | ||
| 15:00 | FK Kožuf | - | Akademija Pandev | 0:2 (0:0) | ||
| 15:00 | FK Ohrid | - | FK Detonit Plačkovica | 2:0 (1:0) | ||
| 15:00 | FK Belasica | - | KF Gostivari | 0:3 (0:0) pn. | ||
| 15:00 | BVK Konjare | - | KF Shkupi | 0:8 (0:3) | ||
| 15:00 | KF Besa Dobërdoll | - | Vardar Skopje | 4:5 (1:1) pn. | ||
| 15:00 | FK Teteks | - | FK Rabotnički | 0:3 (0:0) | ||
| 15:00 | FK Vlazrimi 77 | - | FK Pelister | 0:4 (0:2) | ||
| 15:00 | Karbinci | - | FK Voska Sport | 0:10 (0:4) |
