| Time | Status | Match | FT | H1 | Stats |
| 20/08/2023 17:00 |
(FT) | Bregalnica Stip[7] Fk Rinija Gostivar[12] |
2 1 |
1 0 |
MF | ME |
| 20/08/2023 17:00 |
(FT) | Rabotnicki Skopje[6] FK Makedonija[8] |
1 0 |
1 0 |
MF | ME |
| 20/08/2023 17:00 |
(FT) | Korzo Prilep[9] Sileks[4] |
1 1 |
1 0 |
MF | ME |
| 20/08/2023 17:00 |
(FT) | Tikves Kavadarci[1] FK Shkendija 79[5] |
1 2 |
1 2 |
MF | ME |
| 20/08/2023 17:00 |
(FT) | Voska Sport[11] Vardar Skopje[10] |
3 2 |
2 0 |
MF | ME |
| 21/08/2023 17:00 |
(FT) | Struga Trim Lum[3] Brera Strumica[2] |
1 2 |
0 1 |
MF | ME |