| 1. Ronde | 10.08.2008 | Botev Plovdiv | - | PSFC Chernomorets | 0:1 | ||||
| 2. Ronde | 16.08.2008 | Lokomotiv Plovdiv | - | PSFC Chernomorets | 1:1 | ||||
| 4. Ronde | 31.08.2008 | Cherno More Varna | - | PSFC Chernomorets | 0:1 |  |
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| 5. Ronde | 13.09.2008 | PSFC Chernomorets | - | Lokomotiv Sofia | 1:1 | ||||
| 6. Ronde | 21.09.2008 | PFC Litex Lovech | - | PSFC Chernomorets | 2:2 | ||||
| 7. Ronde | 27.09.2008 | PSFC Chernomorets | - | Lokomotiv 2012 Mezdra | 2:2 | ||||
| 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 | |
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| 19. Ronde | 21.03.2009 | PSFC Chernomorets | - | Cherno More Varna | 0:0 |
Bulgarije