| 8. Round | 04/10/2008 | Spartak Varna | - | FC Pirin | 2:0 | ||||
| 9. Round | 21/10/2008 | FC Pirin | - | Slavia Sofia | 3:2 | ||||
| 11. Round | 01/11/2008 | FC Pirin | - | Lokomotiv Plovdiv | 1:0 | ||||
| 13. Round | 15/11/2008 | Botev Plovdiv | - | FC Pirin | 1:0 |  |
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| 15. Round | 29/11/2008 | Levski Sofia | - | FC Pirin | 2:0 | |
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| 16. Round | 08/03/2009 | Cherno More Varna | - | Pirin Blagoevgrad | 1:0 | ||||
| 20. Round | 05/04/2009 | Belasitsa Petrich | - | Pirin Blagoevgrad | 1:4 | ||||
| 21. Round | 12/04/2009 | Pirin Blagoevgrad | - | OFC Sliven | 3:1 | ||||
| 22. Round | 18/04/2009 | CSKA Sofia | - | Pirin Blagoevgrad | 4:1 | ||||
| 24. Round | 25/04/2009 | Slavia Sofia | - | Pirin Blagoevgrad | 2:3 | ||||
| 25. Round | 03/05/2009 | Pirin Blagoevgrad | - | Minyor Pernik | 1:0 |  |
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| 26. Round | 11/05/2009 | Lokomotiv Plovdiv | - | Pirin Blagoevgrad | 3:2 | |
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| 28. Round | 23/05/2009 | Pirin Blagoevgrad | - | Botev Plovdiv | 0:3 | ||||
| 29. Round | 31/05/2009 | PSFC Chernomorets | - | Pirin Blagoevgrad | 3:1 | ||||
| 30. Round | 13/06/2009 | Pirin Blagoevgrad | - | Levski Sofia | 1:1 | |
Bulgaria