| Time | Status | Match | FT | H1 | Stats | |
| 20/09/2023 15:00 |
(FT) | Ohrid 2004 Detonit Plackovica |
2 0 |
1 0 |
MF | ME | |
| 20/09/2023 15:00 |
(FT) | Kf Arsimi Tikves Kavadarci |
1 2 |
0 2 |
MF | ME | |
| 20/09/2023 15:00 |
(FT) | Bashkimi Skopje |
1 1 |
0 1 |
MF | ME | |
| 90 minutes[1-1], Penalty Kicks[4-3] | ||||||
| 20/09/2023 15:00 |
(FT) | Belasica Strumica Fk Rinija Gostivar |
0 0 |
0 0 |
MF | ME | |
| 90 minutes[0-0], Penalty Kicks[0-3] | ||||||
| 20/09/2023 15:00 |
(FT) | Besa Doberdoll Vardar Skopje |
1 1 |
1 1 |
MF | ME | |
| 90 minutes[1-1], Penalty Kicks[4-5] | ||||||
| 20/09/2023 15:00 |
(FT) | Bratstvo Vlaznimi Korzo Prilep |
0 8 |
0 3 |
MF | ME | |
| 20/09/2023 15:00 |
(FT) | Karbinci Voska Sport |
0 10 |
0 4 |
MF | ME | |
| 20/09/2023 15:00 |
(FT) | Kozuv Brera Strumica |
0 2 |
0 0 |
MF | ME | |
| 20/09/2023 15:00 |
(FT) | Novaci Bregalnica Stip |
0 8 |
0 4 |
MF | ME | |
| 20/09/2023 15:00 |
(FT) | FK Teteks Tetovo Rabotnicki Skopje |
0 3 |
0 0 |
MF | ME | |
| 20/09/2023 15:00 |
(FT) | Vlazrimi Kicevo Pelister Bitola |
0 4 |
0 2 |
MF | ME | |
| 20/09/2023 15:00 |
(FT) | Young Team Struga Pobeda Prilep |
0 0 |
0 0 |
MF | ME | |
| 90 minutes[0-0], Penalty Kicks[4-3] | ||||||