| Time | Status | Match | FT | H1 | Stats | |
| 25/10/2023 14:00 |
(FT) | Bregalnica Stip[MKD D1-8] Young Team Struga |
11 0 |
6 0 |
MF | ME | |
| 25/10/2023 14:00 |
(FT) | Brera Strumica[MKD D1-5] Fk Rinija Gostivar[MKD D1-11] |
0 0 |
0 0 |
MF | ME | |
| 90 minutes[0-0], Penalty Kicks[5-4] | ||||||
| 25/10/2023 14:00 |
(FT) | Pelister Bitola[MKD D2-2] Tikves Kavadarci[MKD D1-6] |
0 1 |
0 0 |
MF | ME | |
| 25/10/2023 14:00 |
(FT) | Rabotnicki Skopje[MKD D1-7] FK Shkendija 79[MKD D1-1] |
3 2 |
1 2 |
MF | ME | |
| 25/10/2023 14:00 |
(FT) | Korzo Prilep[MKD D1-2] Ohrid 2004[MKD D2-5] |
4 0 |
1 0 |
MF | ME | |
| 25/10/2023 14:00 |
(FT) | Sileks[MKD D1-4] Bashkimi[MKD D2-6] |
3 2 |
2 0 |
MF | ME | |
| 25/10/2023 14:00 |
(FT) | Vardar Skopje[MKD D1-12] FK Makedonija[MKD D1-9] |
0 1 |
0 0 |
MF | ME | |
| 25/10/2023 14:00 |
(FT) | Voska Sport[MKD D1-10] Struga Trim Lum[MKD D1-3] |
0 0 |
0 0 |
MF | ME | |
| 90 minutes[0-0], Penalty Kicks[4-1] | ||||||