| 1. Round | 10/08/2015 | FK Bregalnica Štip | - | FK Rabotnički | 1:0 | ||||
| 6. Round | 13/09/2015 | KF Shkupi | - | FK Rabotnički | 1:1 | ||||
| 3. Round | 17/09/2015 | FK Renova | - | FK Rabotnički | 3:1 | ||||
| 7. Round | 20/09/2015 | FK Rabotnički | - | KF Shkëndija 79 | 2:4 |  |
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| 8. Round | 27/09/2015 | Vardar Skopje | - | FK Rabotnički | 2:1 | |
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| 12. Round | 28/10/2015 | FK Rabotnički | - | FK Renova | 1:1 | ||||
| 13. Round | 01/11/2015 | FK Rabotnički | - | Mladost Carev Dvor | 2:0 | |
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| 14. Round | 08/11/2015 | Sileks Kratovo | - | FK Rabotnički | 0:0 | ||||
| 15. Round | 22/11/2015 | FK Rabotnički | - | KF Shkupi | 1:1 | |
North Macedonia