| 1. Round | 08/08/2021 | FK Bregalnica Štip | - | KF Shkupi | 0:0 | ||||
| 2. Round | 15/08/2021 | FK Skopje | - | FK Bregalnica Štip | 0:0 | ||||
| 3. Round | 18/08/2021 | FK Bregalnica Štip | - | KF Shkëndija 79 | 3:3 | ||||
| 4. Round | 22/08/2021 | FK Borec | - | FK Bregalnica Štip | 1:1 | ||||
| 5. Round | 28/08/2021 | FK Bregalnica Štip | - | FK AP Brera Strumica | 3:2 | ||||
| 6. Round | 12/09/2021 | FK Rabotnički | - | FK Bregalnica Štip | 2:0 | ||||
| 7. Round | 19/09/2021 | FK Bregalnica Štip | - | GFK Tikvesh | 2:0 | ||||
| 8. Round | 26/09/2021 | FK Renova | - | FK Bregalnica Štip | 5:2 | ||||
| 9. Round | 02/10/2021 | FK Bregalnica Štip | - | FC Struga | 1:0 |  |
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| 11. Round | 24/10/2021 | FK Pelister | - | FK Bregalnica Štip | 0:3 | ||||
| 12. Round | 29/10/2021 | KF Shkupi | - | FK Bregalnica Štip | 5:0 | ||||
| 16. Round | 05/12/2021 | FK AP Brera Strumica | - | FK Bregalnica Štip | 0:0 | ||||
| 17. Round | 08/12/2021 | FK Bregalnica Štip | - | FK Rabotnički | 1:2 |
North Macedonia