| 1. Round | 10/08/2008 | CSKA Sofia | - | Belasitsa Petrich | 1:0 | ||||
| 2. Round | 15/08/2008 | OFC Sliven | - | CSKA Sofia | 3:1 | ||||
| 4. Round | 30/08/2008 | CSKA Sofia | - | Spartak Varna | 3:0 |  |
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| 8. Round | 04/10/2008 | CSKA Sofia | - | Vihren Sandanski | 2:0 | |
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| 9. Round | 19/10/2008 | Botev Plovdiv | - | CSKA Sofia | 0:2 | ||||
| 11. Round | 01/11/2008 | Levski Sofia | - | CSKA Sofia | 1:1 | ||||
| 12. Round | 08/11/2008 | CSKA Sofia | - | Cherno More Varna | 1:1 | ||||
| 17. Round | 14/03/2009 | CSKA Sofia | - | OFC Sliven | 3:0 | |
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| 18. Round | 18/03/2009 | Lokomotiv Plovdiv | - | CSKA Sofia | 1:3 | ||||
| 19. Round | 21/03/2009 | Spartak Varna | - | CSKA Sofia | 0:2 | ||||
| 20. Round | 05/04/2009 | CSKA Sofia | - | Slavia Sofia | 2:1 | ||||
| 21. Round | 11/04/2009 | Minyor Pernik | - | CSKA Sofia | 0:1 | ||||
| 22. Round | 18/04/2009 | CSKA Sofia | - | Pirin Blagoevgrad | 4:1 | ||||
| 23. Round | 22/04/2009 | Vihren Sandanski | - | CSKA Sofia | 1:4 | ||||
| 24. Round | 26/04/2009 | CSKA Sofia | - | Botev Plovdiv | 2:1 | ||||
| 25. Round | 02/05/2009 | PSFC Chernomorets | - | CSKA Sofia | 0:1 | ||||
| 26. Round | 09/05/2009 | CSKA Sofia | - | Levski Sofia | 0:2 |  |
Nigeria
Bulgaria