| 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 | ||||
| 8. Round | 04/10/2008 | CSKA Sofia | - | Vihren Sandanski | 2:0 | ||||
| 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 |  |
 |
||
| 12. Round | 08/11/2008 | CSKA Sofia | - | Cherno More Varna | 1:1 | ||||
| 13. Round | 15/11/2008 | Lokomotiv Sofia | - | CSKA Sofia | 1:1 | |
|
||
| 14. Round | 23/11/2008 | CSKA Sofia | - | PFC Litex Lovech | 2:0 | ||||
| 20. Round | 05/04/2009 | CSKA Sofia | - | Slavia Sofia | 2:1 | ||||
| 23. Round | 22/04/2009 | Vihren Sandanski | - | CSKA Sofia | 1:4 | ||||
| 24. Round | 26/04/2009 | CSKA Sofia | - | Botev Plovdiv | 2:1 | ||||
| 26. Round | 09/05/2009 | CSKA Sofia | - | Levski Sofia | 0:2 | ||||
| 27. Round | 16/05/2009 | Cherno More Varna | - | CSKA Sofia | 1:0 |
Bulgaria