| 1. Round | 10/08/2008 | CSKA Sofia | - | Belasitsa Petrich | 1:0 | ||||
| 2. Round | 15/08/2008 | OFC Sliven | - | CSKA Sofia | 3:1 | ||||
| 3. Round | 24/08/2008 | CSKA Sofia | - | Lokomotiv Plovdiv | 2:0 | ||||
| 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 | ||||
| 8. Round | 04/10/2008 | CSKA Sofia | - | Vihren Sandanski | 2:0 | ||||
| 10. Round | 25/10/2008 | CSKA Sofia | - | PSFC Chernomorets | 2:1 | ||||
| 12. Round | 08/11/2008 | CSKA Sofia | - | Cherno More Varna | 1:1 | ||||
| 16. Round | 07/03/2009 | Belasitsa Petrich | - | CSKA Sofia | 0:3 | ||||
| 24. Round | 26/04/2009 | CSKA Sofia | - | Botev Plovdiv | 2:1 | ||||
| 29. Round | 31/05/2009 | PFC Litex Lovech | - | CSKA Sofia | 1:0 | ||||
| 30. Round | 13/06/2009 | CSKA Sofia | - | Lokomotiv 2012 Mezdra | 2:1 |
Bulgaria