| 1. Round | 07/08/2016 | FK Bregalnica Štip | - | FK Renova | 1:1 |  |
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| 3. Round | 21/08/2016 | FK Bregalnica Štip | - | Sileks Kratovo | 0:2 | ||||
| 4. Round | 27/08/2016 | Vardar Skopje | - | FK Bregalnica Štip | 5:1 | |
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| 8. Round | 28/09/2016 | FK Bregalnica Štip | - | Makedonija GP | 1:2 | |
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| 9. Round | 01/10/2016 | FK Rabotnički | - | FK Bregalnica Štip | 1:1 | |
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| 35. Round | 28/05/2017 | Makedonija GP | - | FK Bregalnica Štip | 5:3 | ||||
| 36. Round | 31/05/2017 | FK Bregalnica Štip | - | FK Rabotnički | 6:2 |
North Macedonia