| 1. Round | 09/08/2009 | PSFC Chernomorets | - | Cherno More Varna | 2:1 |  |
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| 2. Round | 16/08/2009 | Cherno More Varna | - | OFC Sliven | 4:0 | ||||
| 3. Round | 24/08/2009 | Lokomotiv Plovdiv | - | Cherno More Varna | 1:0 | ||||
| 4. Round | 30/08/2009 | Cherno More Varna | - | Botev Plovdiv | 3:0 |  |
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| 5. Round | 13/09/2009 | PFC Beroe | - | Cherno More Varna | 0:0 | |
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| 11. Round | 30/10/2009 | Pirin Blagoevgrad | - | Cherno More Varna | 1:0 | ||||
| 13. Round | 21/11/2009 | Levski Sofia | - | Cherno More Varna | 3:0 |
Bulgaria