| Time | Status | Match | FT | H1 | Stats | |
| 20/10/2021 14:00 |
(FT) | Belasica Strumica[MKD D2E-4] Sileks[MKD D2W-1] |
2 4 |
0 3 |
MF | ME | |
| 20/10/2021 14:00 |
(FT) | Pelister Bitola[MKD D1-12] Rabotnicki Skopje[MKD D1-5] |
0 0 |
0 0 |
MF | ME | |
| 90 minutes[0-0], Penalty Kicks[5-4] | ||||||
| 20/10/2021 14:00 |
(FT) | Brera Strumica[MKD D1-3] FK Makedonija[MKD D1-9] |
1 1 |
0 0 |
MF | ME | |
| 90 minutes[1-1], Penalty Kicks[3-5] | ||||||
| 20/10/2021 14:00 |
(FT) | Struga Trim Lum[MKD D1-7] Borec Veles[MKD D1-10] |
1 1 |
1 1 |
MF | ME | |
| 90 minutes[1-1], Penalty Kicks[5-4] | ||||||
| 20/10/2021 14:00 |
(FT) | Vardar Skopje[MKD D2W-4] Skopje[MKD D1-8] |
0 0 |
0 0 |
MF | ME | |
| 90 minutes[0-0], Penalty Kicks[4-2] | ||||||
| 20/10/2021 14:00 |
(FT) | Bregalnica Stip[MKD D1-4] Ohrid 2004[MKD D2W-10] |
4 0 |
1 0 |
MF | ME | |
| 20/10/2021 14:00 |
(FT) | FK Shkendija 79[MKD D1-6] Renova Cepciste[MKD D1-2] |
5 0 |
4 0 |
MF | ME | |
| 20/10/2021 14:00 |
(FT) | Korzo Prilep[MKD D1-1] Tikves Kavadarci[MKD D1-11] |
1 0 |
1 0 |
MF | ME | |