| 1. Round | 09/08/2008 | OFC Sliven | - | Lokomotiv Plovdiv | 1:1 | ||||
| 2. Round | 15/08/2008 | OFC Sliven | - | CSKA Sofia | 3:1 |  |
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| 4. Round | 30/08/2008 | OFC Sliven | - | Slavia Sofia | 1:1 | ||||
| 6. Round | 20/09/2008 | OFC Sliven | - | FC Pirin | 2:1 | ||||
| 7. Round | 29/09/2008 | Vihren Sandanski | - | OFC Sliven | 0:2 | ||||
| 8. Round | 04/10/2008 | OFC Sliven | - | Botev Plovdiv | 3:1 | ||||
| 9. Round | 20/10/2008 | PSFC Chernomorets | - | OFC Sliven | 1:1 | ||||
| 10. Round | 26/10/2008 | OFC Sliven | - | Levski Sofia | 0:0 | ||||
| 11. Round | 01/11/2008 | Cherno More Varna | - | OFC Sliven | 3:0 | ||||
| 12. Round | 08/11/2008 | OFC Sliven | - | Lokomotiv Sofia | 0:0 | ||||
| 13. Round | 15/11/2008 | PFC Litex Lovech | - | OFC Sliven | 2:0 | ||||
| 17. Round | 14/03/2009 | CSKA Sofia | - | OFC Sliven | 3:0 | ||||
| 18. Round | 18/03/2009 | OFC Sliven | - | Spartak Varna | 0:1 | ||||
| 30. Round | 13/06/2009 | OFC Sliven | - | Belasitsa Petrich | 0:2 |
Bulgaria