| 1. Round | 10/08/2008 | Botev Plovdiv | - | PSFC Chernomorets | 0:1 | ||||
| 2. Round | 16/08/2008 | Lokomotiv Plovdiv | - | PSFC Chernomorets | 1:1 |  |
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| 4. Round | 31/08/2008 | Cherno More Varna | - | PSFC Chernomorets | 0:1 | ||||
| 6. Round | 21/09/2008 | PFC Litex Lovech | - | PSFC Chernomorets | 2:2 |  |
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| 7. Round | 27/09/2008 | PSFC Chernomorets | - | Lokomotiv 2012 Mezdra | 2:2 | |
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| 8. Round | 04/10/2008 | Belasitsa Petrich | - | PSFC Chernomorets | 0:1 | |
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| 14. Round | 23/11/2008 | FC Pirin | - | PSFC Chernomorets | 2:1 | |
Bulgaria