| 4. Round | 20/08/2016 | Pirin Blagoevgrad | - | CSKA Sofia | 1:1 |  |
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| 5. Round | 26/08/2016 | PFC Beroe | - | Pirin Blagoevgrad | 1:0 | ||||
| 8. Round | 23/09/2016 | Pirin Blagoevgrad | - | PFC Montana | 1:0 | ||||
| 9. Round | 30/09/2016 | Lokomotiv Plovdiv | - | Pirin Blagoevgrad | 2:3 | ||||
| 10. Round | 14/10/2016 | Pirin Blagoevgrad | - | PFC Ludogorets Razgrad | 1:3 | |
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| 11. Round | 23/10/2016 | Slavia Sofia | - | Pirin Blagoevgrad | 3:1 | ||||
| 12. Round | 31/10/2016 | Pirin Blagoevgrad | - | FK Vereya | 1:1 | ||||
| 13. Round | 04/11/2016 | Neftochimik Burgas | - | Pirin Blagoevgrad | 3:1 | ||||
| 14. Round | 18/11/2016 | Cherno More Varna | - | Pirin Blagoevgrad | 0:0 | |
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| 15. Round | 25/11/2016 | Lokomotiv Gorna Oryahovitsa | - | Pirin Blagoevgrad | 1:0 | ||||
| 16. Round | 30/11/2016 | Pirin Blagoevgrad | - | FC Dunav Ruse | 4:1 | ||||
| 17. Round | 04/12/2016 | CSKA Sofia | - | Pirin Blagoevgrad | 2:0 | ||||
| 18. Round | 12/12/2016 | Pirin Blagoevgrad | - | PFC Beroe | 1:1 | ||||
| 19. Round | 15/12/2016 | Botev Plovdiv | - | Pirin Blagoevgrad | 3:2 |
Bulgaria