| Time | Status | Match | FT | H1 | Stats | |
| 01/12/2021 13:00 |
(FT) | Sileks[MKD D2W-1] Bregalnica Stip[MKD D1-6] |
1 1 |
0 0 |
MF | ME | |
| 90 minutes[1-1], Penalty Kicks[5-4] | ||||||
| 01/12/2021 13:00 |
(FT) | FK Shkendija 79[MKD D1-4] Struga Trim Lum[MKD D1-5] |
0 0 |
0 0 |
MF | ME | |
| 90 minutes[0-0], Penalty Kicks[3-4] | ||||||
| 01/12/2021 13:00 |
(FT) | FK Makedonija[MKD D1-7] Korzo Prilep[MKD D1-1] |
0 0 |
0 0 |
MF | ME | |
| 90 minutes[0-0], Penalty Kicks[4-1] | ||||||
| 15/12/2021 13:00 |
(FT) | Pelister Bitola[MKD D1-12] Vardar Skopje[MKD D2W-3] |
0 0 |
0 0 |
MF | ME | |
| 90 minutes[0-0], Penalty Kicks[3-2] | ||||||