| 1. Journée | 10.08.2008 | Botev Plovdiv | - | PSFC Chernomorets | 0:1 | ||||
| 2. Journée | 16.08.2008 | Lokomotiv Plovdiv | - | PSFC Chernomorets | 1:1 |  |
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| 4. Journée | 31.08.2008 | Cherno More Varna | - | PSFC Chernomorets | 0:1 | ||||
| 6. Journée | 21.09.2008 | PFC Litex Lovech | - | PSFC Chernomorets | 2:2 |  |
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| 7. Journée | 27.09.2008 | PSFC Chernomorets | - | Lokomotiv 2012 Mezdra | 2:2 | |
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| 8. Journée | 04.10.2008 | Belasitsa Petrich | - | PSFC Chernomorets | 0:1 | |
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| 14. Journée | 23.11.2008 | FC Pirin | - | PSFC Chernomorets | 2:1 | |
Bulgarie