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GMT 02:00
| 27.09.2023 | |||
| 15:00 | Voska Sport | 0-1 | FC Struga |
| 24.09.2023 | |||
| 15:00 | AP Brera Strumica | 1-1 | Sileks Kratovo |
| 15:00 | FC Struga | 1-0 | Rabotnicki Skopje |
| 15:00 | Shkendija'79 | 1-0 | Makedonija GP |
| 15:00 | Tikves Kavadarci | 2-1 | Bregalnica Stip |
| 15:00 | Vardar Skopje | 0-2 | Gostivari |
| 15:00 | Voska Sport | 2-3 | Shkupi |
| 17.09.2023 | |||
| 15:00 | Bregalnica Stip | 1-3 | FC Struga |
| 15:00 | Makedonija GP | 3-0 | Gostivari |
| 15:00 | Rabotnicki Skopje | 2-0 | Voska Sport |
| 15:00 | Sileks Kratovo | 2-1 | Shkendija'79 |
| 15:00 | Tikves Kavadarci | 1-0 | Vardar Skopje |
| 30.09.2023 | ||||
| 14:00 | Makedonija GP | - | AP Brera Strumica | |
| 01.10.2023 | ||||
| 14:00 | Bregalnica Stip | - | Vardar Skopje | |
| 14:00 | Gostivari | - | Shkendija'79 | |
| 14:00 | Rabotnicki Skopje | - | Tikves Kavadarci | |
| 14:00 | Shkupi | - | FC Struga | |
| 14:00 | Sileks Kratovo | - | Voska Sport | |
| 04.10.2023 | ||||
| 14:00 | Shkendija'79 | - | FC Struga | |
| 07.10.2023 | ||||
| 14:00 | AP Brera Strumica | - | Gostivari | |
| 14:00 | Bregalnica Stip | - | Rabotnicki Skopje | |
| 14:00 | FC Struga | - | Sileks Kratovo | |
| 14:00 | Tikves Kavadarci | - | Shkupi | |
| 14:00 | Vardar Skopje | - | Shkendija'79 | |
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