| 4. Ronde | 31.08.2008 | Cherno More Varna | - | PSFC Chernomorets | 0:1 | ||||
| 5. Ronde | 13.09.2008 | PSFC Chernomorets | - | Lokomotiv Sofia | 1:1 |  |
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| 6. Ronde | 21.09.2008 | PFC Litex Lovech | - | PSFC Chernomorets | 2:2 | ||||
| 7. Ronde | 27.09.2008 | PSFC Chernomorets | - | Lokomotiv 2012 Mezdra | 2:2 | |
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| 8. Ronde | 04.10.2008 | Belasitsa Petrich | - | PSFC Chernomorets | 0:1 | ||||
| 9. Ronde | 20.10.2008 | PSFC Chernomorets | - | OFC Sliven | 1:1 | ||||
| 10. Ronde | 25.10.2008 | CSKA Sofia | - | PSFC Chernomorets | 2:1 |  |
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| 11. Ronde | 31.10.2008 | PSFC Chernomorets | - | Spartak Varna | 2:0 | |
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| 3. Ronde | 05.11.2008 | PSFC Chernomorets | - | Levski Sofia | 2:2 | |
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| 14. Ronde | 23.11.2008 | FC Pirin | - | PSFC Chernomorets | 2:1 | ||||
| 15. Ronde | 29.11.2008 | PSFC Chernomorets | - | Vihren Sandanski | 1:3 | ||||
| 16. Ronde | 07.03.2009 | PSFC Chernomorets | - | Botev Plovdiv | 2:1 | ||||
| 17. Ronde | 15.03.2009 | PSFC Chernomorets | - | Lokomotiv Plovdiv | 1:3 | ||||
| 18. Ronde | 18.03.2009 | Levski Sofia | - | PSFC Chernomorets | 3:1 | ||||
| 19. Ronde | 21.03.2009 | PSFC Chernomorets | - | Cherno More Varna | 0:0 | ||||
| 27. Ronde | 16.05.2009 | PSFC Chernomorets | - | Slavia Sofia | 2:1 |
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