| 4. Round | 31/08/2008 | Cherno More Varna | - | PSFC Chernomorets | 0:1 | ||||
| 5. Round | 13/09/2008 | PSFC Chernomorets | - | Lokomotiv Sofia | 1:1 |  |
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| 6. Round | 21/09/2008 | PFC Litex Lovech | - | PSFC Chernomorets | 2:2 | ||||
| 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 | ||||
| 9. Round | 20/10/2008 | PSFC Chernomorets | - | OFC Sliven | 1:1 | ||||
| 10. Round | 25/10/2008 | CSKA Sofia | - | PSFC Chernomorets | 2:1 |  |
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| 11. Round | 31/10/2008 | PSFC Chernomorets | - | Spartak Varna | 2:0 | |
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| 3. Round | 05/11/2008 | PSFC Chernomorets | - | Levski Sofia | 2:2 | |
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| 14. Round | 23/11/2008 | FC Pirin | - | PSFC Chernomorets | 2:1 | ||||
| 15. Round | 29/11/2008 | PSFC Chernomorets | - | Vihren Sandanski | 1:3 | ||||
| 16. Round | 07/03/2009 | PSFC Chernomorets | - | Botev Plovdiv | 2:1 | ||||
| 17. Round | 15/03/2009 | PSFC Chernomorets | - | Lokomotiv Plovdiv | 1:3 | ||||
| 18. Round | 18/03/2009 | Levski Sofia | - | PSFC Chernomorets | 3:1 | ||||
| 19. Round | 21/03/2009 | PSFC Chernomorets | - | Cherno More Varna | 0:0 | ||||
| 27. Round | 16/05/2009 | PSFC Chernomorets | - | Slavia Sofia | 2:1 |
Serbia