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| 15.09.2021 | 15:00 | FK Detonit Junior | - | Makedonija GP | 0:3 | |
| 15:00 | FK Pobeda Junior | - | Vardar Skopje | 4:5 i.E. | ||
| 15:00 | KF Besa Dobërdoll | - | FK Skopje | 4:5 (0:0, 1:1) i.E. | ||
| 15:00 | Lokomotiva Gradsko | - | FK Ohrid | 0:2 | ||
| 15:00 | KF Gostivari | - | FK Renova | 0:4 | ||
| 15:00 | FK Ljuboten | - | FK Pelister | 0:9 | ||
| 15:00 | KF Korabi | - | FK Belasica | 1:2 | ||
| 15:00 | FK Sloga 1934 | - | FK Rabotnički | 0:3 | ||
| 15:00 | FK Novaci 2005 | - | GFK Tikvesh | 0:2 | ||
| 15:00 | Kamenica Sasa | - | FC Struga | 0:2 | ||
| 15:00 | FK Voska Sport | - | FK Bregalnica Štip | 0:1 | ||
| 22.09.2021 | 15:00 | FK Kit-Go Pehčevo | - | KF Shkëndija 79 | 0:2 | |
| 15:00 | FK New Stars | - | FK Borec | 1:4 | ||
| 15:00 | KF Veleshta | - | KF Shkupi | 0:1 |
