| 1. Round | 10/08/2008 | CSKA Sofia | - | Belasitsa Petrich | 1:0 | ||||
| 2. Round | 16/08/2008 | Belasitsa Petrich | - | Spartak Varna | 0:0 | ||||
| 3. Round | 24/08/2008 | Slavia Sofia | - | Belasitsa Petrich | 3:0 |  |
|||
| 6. Round | 22/09/2008 | Belasitsa Petrich | - | Vihren Sandanski | 1:2 | ||||
| 7. Round | 27/09/2008 | Botev Plovdiv | - | Belasitsa Petrich | 5:0 | ||||
| 9. Round | 18/10/2008 | Levski Sofia | - | Belasitsa Petrich | 2:0 | ||||
| 10. Round | 26/10/2008 | Belasitsa Petrich | - | Cherno More Varna | 2:0 | ||||
| 11. Round | 02/11/2008 | Lokomotiv Sofia | - | Belasitsa Petrich | 3:1 | ||||
| 19. Round | 23/03/2009 | Minyor Pernik | - | Belasitsa Petrich | 0:3 | ||||
| 21. Round | 10/04/2009 | Vihren Sandanski | - | Belasitsa Petrich | 4:1 | ||||
| 23. Round | 23/04/2009 | PSFC Chernomorets | - | Belasitsa Petrich | 2:0 | ||||
| 26. Round | 10/05/2009 | Belasitsa Petrich | - | Lokomotiv Sofia | 2:4 | ||||
| 28. Round | 23/05/2009 | Belasitsa Petrich | - | Lokomotiv 2012 Mezdra | 1:3 | ||||
| 29. Round | 31/05/2009 | Belasitsa Petrich | - | Lokomotiv Plovdiv | 1:2 | ||||
| 30. Round | 13/06/2009 | OFC Sliven | - | Belasitsa Petrich | 0:2 |
Bulgaria