| 5. Jornada | 13.09.2008 | PSFC Chernomorets | - | Lokomotiv Sofia | 1:1 |  |
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| 9. Jornada | 20.10.2008 | PSFC Chernomorets | - | OFC Sliven | 1:1 | ||||
| 10. Jornada | 25.10.2008 | CSKA Sofia | - | PSFC Chernomorets | 2:1 | ||||
| 11. Jornada | 31.10.2008 | PSFC Chernomorets | - | Spartak Varna | 2:0 | ||||
| 3. Jornada | 05.11.2008 | PSFC Chernomorets | - | Levski Sofia | 2:2 | |
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| 12. Jornada | 10.11.2008 | Slavia Sofia | - | PSFC Chernomorets | 2:0 | ||||
| 13. Jornada | 17.11.2008 | PSFC Chernomorets | - | Minyor Pernik | 1:1 | ||||
| 14. Jornada | 23.11.2008 | FC Pirin | - | PSFC Chernomorets | 2:1 | ||||
| 20. Jornada | 04.04.2009 | Lokomotiv Sofia | - | PSFC Chernomorets | 2:0 | ||||
| 23. Jornada | 23.04.2009 | PSFC Chernomorets | - | Belasitsa Petrich | 2:0 |  |
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| 24. Jornada | 27.04.2009 | OFC Sliven | - | PSFC Chernomorets | 0:0 | ||||
| 28. Jornada | 23.05.2009 | Minyor Pernik | - | PSFC Chernomorets | 1:0 | ||||
| 29. Jornada | 31.05.2009 | PSFC Chernomorets | - | Pirin Blagoevgrad | 3:1 |
Bulgaria