| Time | Status | Match | FT | H1 | Stats | |
| 20/09/2023 14:00 |
(FT) | Ohrid 2004 Detonit Plackovica |
2 0 |
1 0 |
MF | ME | |
| 20/09/2023 14:00 |
(FT) | Kf Arsimi[MKD D2-10] Tikves Kavadarci[MKD D1-5] |
1 2 |
0 2 |
MF | ME | |
| 20/09/2023 14:00 |
(FT) | Bashkimi[MKD D2-6] Skopje[MKD D2-13] |
1 1 |
0 1 |
MF | ME | |
| 90 minutes[1-1], Penalty Kicks[4-3] | ||||||
| 20/09/2023 14:00 |
(FT) | Belasica Strumica[MKD D2-5] Fk Rinija Gostivar[MKD D1-12] |
0 0 |
0 0 |
MF | ME | |
| 90 minutes[0-0], Penalty Kicks[0-3] | ||||||
| 20/09/2023 14:00 |
(FT) | Besa Doberdoll[MKD D2-2] Vardar Skopje[MKD D1-11] |
1 1 |
1 1 |
MF | ME | |
| 90 minutes[1-1], Penalty Kicks[4-5] | ||||||
| 20/09/2023 14:00 |
(FT) | Bratstvo Vlaznimi Korzo Prilep[MKD D1-4] |
0 8 |
0 3 |
MF | ME | |
| 20/09/2023 14:00 |
(FT) | Karbinci Voska Sport[MKD D1-10] |
0 10 |
0 4 |
MF | ME | |
| 20/09/2023 14:00 |
(FT) | Kozuv[MKD D2-1] Brera Strumica[MKD D1-2] |
0 2 |
0 0 |
MF | ME | |
| 20/09/2023 14:00 |
(FT) | Novaci[MKD D2-7] Bregalnica Stip[MKD D1-8] |
0 8 |
0 4 |
MF | ME | |
| 20/09/2023 14:00 |
(FT) | FK Teteks Tetovo[MKD D2-12] Rabotnicki Skopje[MKD D1-6] |
0 3 |
0 0 |
MF | ME | |
| 20/09/2023 14:00 |
(FT) | Vlazrimi Kicevo Pelister Bitola[MKD D2-4] |
0 4 |
0 2 |
MF | ME | |
| 20/09/2023 14:00 |
(FT) | Young Team Struga Pobeda Prilep[MKD D2-8] |
0 0 |
0 0 |
MF | ME | |
| 90 minutes[0-0], Penalty Kicks[4-3] | ||||||