| 1. Round | 10/08/2008 | CSKA Sofia | - | Belasitsa Petrich | 1:0 |  |
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| 2. Round | 15/08/2008 | OFC Sliven | - | CSKA Sofia | 3:1 | ||||
| 3. Round | 24/08/2008 | CSKA Sofia | - | Lokomotiv Plovdiv | 2:0 | |
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| 4. Round | 30/08/2008 | CSKA Sofia | - | Spartak Varna | 3:0 | ||||
| 5. Round | 14/09/2008 | Slavia Sofia | - | CSKA Sofia | 1:2 | ||||
| 6. Round | 19/09/2008 | CSKA Sofia | - | Minyor Pernik | 2:0 | ||||
| 7. Round | 27/09/2008 | FC Pirin | - | CSKA Sofia | 2:2 | ||||
| 9. Round | 19/10/2008 | Botev Plovdiv | - | CSKA Sofia | 0:2 | ||||
| 10. Round | 25/10/2008 | CSKA Sofia | - | PSFC Chernomorets | 2:1 | ||||
| 11. Round | 01/11/2008 | Levski Sofia | - | CSKA Sofia | 1:1 |  |
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| 13. Round | 15/11/2008 | Lokomotiv Sofia | - | CSKA Sofia | 1:1 | ||||
| 14. Round | 23/11/2008 | CSKA Sofia | - | PFC Litex Lovech | 2:0 | ||||
| 15. Round | 28/11/2008 | Lokomotiv 2012 Mezdra | - | CSKA Sofia | 2:2 |
Bulgaria