| 2. Jornada | 16.08.2009 | PFC Litex Lovech | - | Pirin Blagoevgrad | 0:1 | ||||
| 3. Jornada | 22.08.2009 | Pirin Blagoevgrad | - | Slavia Sofia | 1:0 | ||||
| 6. Jornada | 19.09.2009 | PSFC Chernomorets | - | Pirin Blagoevgrad | 2:1 |  |
|||
| 8. Jornada | 05.10.2009 | PFC Beroe | - | Pirin Blagoevgrad | 1:1 | ||||
| 9. Jornada | 17.10.2009 | Pirin Blagoevgrad | - | FK Sportist Svoge | 2:0 | |
|||
| 10. Jornada | 24.10.2009 | Lokomotiv 2012 Mezdra | - | Pirin Blagoevgrad | 4:0 | ||||
| 11. Jornada | 30.10.2009 | Pirin Blagoevgrad | - | Cherno More Varna | 1:0 | ||||
| 13. Jornada | 20.11.2009 | PFC Montana | - | Pirin Blagoevgrad | 0:3 | ||||
| 14. Jornada | 27.11.2009 | Pirin Blagoevgrad | - | OFC Sliven | 2:0 | |
|||
| 15. Jornada | 05.12.2009 | Botev Plovdiv | - | Pirin Blagoevgrad | 2:2 |
Bulgaria