| 1. Round | 08/08/2009 | PFC Montana | - | OFC Sliven | 0:0 | ||||
| 2. Round | 16/08/2009 | Cherno More Varna | - | OFC Sliven | 4:0 | ||||
| 4. Round | 29/08/2009 | Minyor Pernik | - | OFC Sliven | 4:2 | ||||
| 5. Round | 13/09/2009 | OFC Sliven | - | PFC Litex Lovech | 1:2 | ||||
| 6. Round | 19/09/2009 | Slavia Sofia | - | OFC Sliven | 2:1 |  |
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| 7. Round | 25/09/2009 | OFC Sliven | - | Lokomotiv Sofia | 1:3 | ||||
| 9. Round | 16/10/2009 | OFC Sliven | - | PSFC Chernomorets | 0:1 | ||||
| 10. Round | 24/10/2009 | Lokomotiv Plovdiv | - | OFC Sliven | 1:2 | ||||
| 11. Round | 02/11/2009 | OFC Sliven | - | PFC Beroe | 1:1 |  |
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| 12. Round | 07/11/2009 | FK Sportist Svoge | - | OFC Sliven | 1:0 |
Bulgaria