| 2. Round | 05/08/2016 | Pirin Blagoevgrad | - | Lokomotiv Gorna Oryahovitsa | 2:1 |  |
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| 5. Round | 26/08/2016 | PFC Beroe | - | Pirin Blagoevgrad | 1:0 | ||||
| 7. Round | 17/09/2016 | Levski Sofia | - | Pirin Blagoevgrad | 2:0 | ||||
| 8. Round | 23/09/2016 | Pirin Blagoevgrad | - | PFC Montana | 1:0 | ||||
| 10. Round | 14/10/2016 | Pirin Blagoevgrad | - | PFC Ludogorets Razgrad | 1:3 | ||||
| 14. Round | 18/11/2016 | Cherno More Varna | - | Pirin Blagoevgrad | 0:0 |
Bulgaria