| 3. Round | 23/08/2015 | FK Bregalnica Štip | - | KF Shkupi | 1:2 | ||||
| 5. Round | 29/08/2015 | FK Bregalnica Štip | - | Vardar Skopje | 0:2 | ||||
| 6. Round | 13/09/2015 | Metalurg Skopje | - | FK Bregalnica Štip | 0:3 | ||||
| 7. Round | 19/09/2015 | FK Bregalnica Štip | - | Mladost Carev Dvor | 2:3 | ||||
| 8. Round | 27/09/2015 | FK Bregalnica Štip | - | FK Turnovo | 3:0 |
North Macedonia