| 2. Round | 15/08/2009 | Botev Plovdiv | - | PFC Montana | 2:3 | ||||
| 7. Round | 26/09/2009 | PFC Montana | - | CSKA Sofia | 1:2 |  |
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| 9. Round | 17/10/2009 | PFC Montana | - | Lokomotiv Plovdiv | 2:3 | ||||
| 10. Round | 23/10/2009 | PFC Beroe | - | PFC Montana | 0:0 | |
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| 11. Round | 31/10/2009 | PFC Montana | - | FK Sportist Svoge | 1:0 | ||||
| 12. Round | 06/11/2009 | Lokomotiv 2012 Mezdra | - | PFC Montana | 0:2 | ||||
| 14. Round | 28/11/2009 | Levski Sofia | - | PFC Montana | 3:1 | ||||
| 21. Round | 29/03/2010 | PFC Montana | - | Lokomotiv Sofia | 0:1 | ||||
| 30. Round | 16/05/2010 | Cherno More Varna | - | PFC Montana | 2:1 |
Bulgaria