| 8. Round | 04/10/2008 | Belasitsa Petrich | - | PSFC Chernomorets | 0:1 |  |
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| 9. Round | 20/10/2008 | PSFC Chernomorets | - | OFC Sliven | 1:1 | ||||
| 10. Round | 25/10/2008 | CSKA Sofia | - | PSFC Chernomorets | 2:1 | ||||
| 11. Round | 31/10/2008 | PSFC Chernomorets | - | Spartak Varna | 2:0 | ||||
| 3. Round | 05/11/2008 | PSFC Chernomorets | - | Levski Sofia | 2:2 | |
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| 12. Round | 10/11/2008 | Slavia Sofia | - | PSFC Chernomorets | 2:0 | ||||
| 13. Round | 17/11/2008 | PSFC Chernomorets | - | Minyor Pernik | 1:1 | ||||
| 14. Round | 23/11/2008 | FC Pirin | - | PSFC Chernomorets | 2:1 | ||||
| 15. Round | 29/11/2008 | PSFC Chernomorets | - | Vihren Sandanski | 1:3 |
Serbia