| 1. Round | 09/08/2008 | Slavia Sofia | - | PFC Litex Lovech | 0:3 | ||||
| 2. Round | 16/08/2008 | Lokomotiv 2012 Mezdra | - | Slavia Sofia | 1:0 | ||||
| 3. Round | 24/08/2008 | Slavia Sofia | - | Belasitsa Petrich | 3:0 | ||||
| 4. Round | 30/08/2008 | OFC Sliven | - | Slavia Sofia | 1:1 | ||||
| 7. Round | 28/09/2008 | Slavia Sofia | - | Lokomotiv Plovdiv | 2:0 |  |
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| 8. Round | 05/10/2008 | Slavia Sofia | - | Minyor Pernik | 1:1 | ||||
| 9. Round | 21/10/2008 | FC Pirin | - | Slavia Sofia | 3:2 | ||||
| 10. Round | 27/10/2008 | Slavia Sofia | - | Vihren Sandanski | 2:0 | ||||
| 11. Round | 03/11/2008 | Botev Plovdiv | - | Slavia Sofia | 2:1 | ||||
| 12. Round | 10/11/2008 | Slavia Sofia | - | PSFC Chernomorets | 2:0 | ||||
| 13. Round | 16/11/2008 | Levski Sofia | - | Slavia Sofia | 1:0 |  |
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| 15. Round | 01/12/2008 | Lokomotiv Sofia | - | Slavia Sofia | 0:1 |
Bulgaria