| 1. Round | 31/07/2010 | Cherno More Varna | - | Pirin Blagoevgrad | 2:1 | ||||
| 2. Round | 07/08/2010 | Pirin Blagoevgrad | - | OFC Sliven | 2:1 | ||||
| 3. Round | 14/08/2010 | PFC Litex Lovech | - | Pirin Blagoevgrad | 2:1 | ||||
| 4. Round | 21/08/2010 | Pirin Blagoevgrad | - | Slavia Sofia | 0:2 | ||||
| 5. Round | 28/08/2010 | PFC Montana | - | Pirin Blagoevgrad | 3:0 | ||||
| 6. Round | 11/09/2010 | Pirin Blagoevgrad | - | Lokomotiv Sofia | 2:1 | ||||
| 7. Round | 18/09/2010 | PFC Kaliakra Kavarna | - | Pirin Blagoevgrad | 0:0 |  |
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| 8. Round | 25/09/2010 | Pirin Blagoevgrad | - | Minyor Pernik | 1:1 | ||||
| 9. Round | 02/10/2010 | PFC Beroe | - | Pirin Blagoevgrad | 0:0 | ||||
| 10. Round | 16/10/2010 | Levski Sofia | - | Pirin Blagoevgrad | 4:1 | ||||
| 11. Round | 23/10/2010 | Pirin Blagoevgrad | - | Lokomotiv Plovdiv | 1:1 | ||||
| 12. Round | 30/10/2010 | Akademik Sofia | - | Pirin Blagoevgrad | 1:0 | ||||
| 13. Round | 08/11/2010 | Pirin Blagoevgrad | - | CSKA Sofia | 0:1 | ||||
| 14. Round | 15/11/2010 | PSFC Chernomorets | - | Pirin Blagoevgrad | 1:0 | ||||
| 15. Round | 27/11/2010 | Pirin Blagoevgrad | - | Vidima Rakovski | 1:1 |
Bulgaria