| 1. Ronde | 08.08.2009 | Pirin Blagoevgrad | - | Minyor Pernik | 0:1 |  |
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| 2. Ronde | 16.08.2009 | PFC Litex Lovech | - | Pirin Blagoevgrad | 0:1 | ||||
| 3. Ronde | 22.08.2009 | Pirin Blagoevgrad | - | Slavia Sofia | 1:0 | ||||
| 4. Ronde | 29.08.2009 | Lokomotiv Sofia | - | Pirin Blagoevgrad | 1:0 | |
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| 5. Ronde | 12.09.2009 | Pirin Blagoevgrad | - | CSKA Sofia | 0:0 | ||||
| 6. Ronde | 19.09.2009 | PSFC Chernomorets | - | Pirin Blagoevgrad | 2:1 | |
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| 7. Ronde | 28.09.2009 | Pirin Blagoevgrad | - | Lokomotiv Plovdiv | 0:0 | ||||
| 8. Ronde | 05.10.2009 | PFC Beroe | - | Pirin Blagoevgrad | 1:1 | ||||
| 9. Ronde | 17.10.2009 | Pirin Blagoevgrad | - | FK Sportist Svoge | 2:0 | ||||
| 10. Ronde | 24.10.2009 | Lokomotiv 2012 Mezdra | - | Pirin Blagoevgrad | 4:0 | ||||
| 11. Ronde | 30.10.2009 | Pirin Blagoevgrad | - | Cherno More Varna | 1:0 | |
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| 12. Ronde | 08.11.2009 | Pirin Blagoevgrad | - | Levski Sofia | 0:2 | |
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| 14. Ronde | 27.11.2009 | Pirin Blagoevgrad | - | OFC Sliven | 2:0 |
Bulgarije