| 1. Round | 09/08/2008 | FC Pirin | - | Cherno More Varna | 1:2 | ||||
| 15. Round | 29/11/2008 | Levski Sofia | - | FC Pirin | 2:0 | ||||
| 16. Round | 08/03/2009 | Cherno More Varna | - | Pirin Blagoevgrad | 1:0 | ||||
| 17. Round | 13/03/2009 | Pirin Blagoevgrad | - | Lokomotiv Sofia | 0:4 | ||||
| 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 | ||||
| 23. Round | 22/04/2009 | Pirin Blagoevgrad | - | Spartak Varna | 0:0 | ||||
| 24. Round | 25/04/2009 | Slavia Sofia | - | Pirin Blagoevgrad | 2:3 | ||||
| 25. Round | 03/05/2009 | Pirin Blagoevgrad | - | Minyor Pernik | 1:0 | ||||
| 26. Round | 11/05/2009 | Lokomotiv Plovdiv | - | Pirin Blagoevgrad | 3:2 | ||||
| 27. Round | 18/05/2009 | Vihren Sandanski | - | Pirin Blagoevgrad | 1:3 |  |
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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 |
Bulgaria