| 1. Round | 09/08/2008 | FC Pirin | - | Cherno More Varna | 1:2 | ||||
| 2. Round | 17/08/2008 | Lokomotiv Sofia | - | FC Pirin | 1:0 | ||||
| 3. Round | 23/08/2008 | FC Pirin | - | PFC Litex Lovech | 1:1 | ||||
| 4. Round | 30/08/2008 | Lokomotiv 2012 Mezdra | - | FC Pirin | 4:0 | ||||
| 5. Round | 15/09/2008 | FC Pirin | - | Belasitsa Petrich | 2:0 | ||||
| 6. Round | 20/09/2008 | OFC Sliven | - | FC Pirin | 2:1 | ||||
| 9. Round | 21/10/2008 | FC Pirin | - | Slavia Sofia | 3:2 | ||||
| 10. Round | 25/10/2008 | Minyor Pernik | - | FC Pirin | 0:0 | ||||
| 12. Round | 07/11/2008 | FC Pirin | - | Vihren Sandanski | 2:1 | ||||
| 15. Round | 29/11/2008 | Levski Sofia | - | FC Pirin | 2:0 | ||||
| 16. Round | 08/03/2009 | Cherno More Varna | - | Pirin Blagoevgrad | 1:0 | ||||
| 18. Round | 19/03/2009 | PFC Litex Lovech | - | Pirin Blagoevgrad | 3:0 | ||||
| 19. Round | 23/03/2009 | Pirin Blagoevgrad | - | Lokomotiv 2012 Mezdra | 1:2 | ||||
| 24. Round | 25/04/2009 | Slavia Sofia | - | Pirin Blagoevgrad | 2:3 | ||||
| 27. Round | 18/05/2009 | Vihren Sandanski | - | Pirin Blagoevgrad | 1:3 | ||||
| 28. Round | 23/05/2009 | Pirin Blagoevgrad | - | Botev Plovdiv | 0:3 | ||||
| 30. Round | 13/06/2009 | Pirin Blagoevgrad | - | Levski Sofia | 1:1 |
Bulgaria