| 5. Round | 15/09/2008 | FC Pirin | - | Belasitsa Petrich | 2:0 | ||||
| 10. Round | 25/10/2008 | Minyor Pernik | - | FC Pirin | 0:0 | ||||
| 13. Round | 15/11/2008 | Botev Plovdiv | - | FC Pirin | 1:0 |  |
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| 18. Round | 19/03/2009 | PFC Litex Lovech | - | Pirin Blagoevgrad | 3:0 | ||||
| 19. Round | 23/03/2009 | Pirin Blagoevgrad | - | Lokomotiv 2012 Mezdra | 1:2 | ||||
| 22. Round | 18/04/2009 | CSKA Sofia | - | Pirin Blagoevgrad | 4:1 |
Bulgaria