| 1. Round | 10/08/2008 | Botev Plovdiv | - | PSFC Chernomorets | 0:1 | ||||
| 2. Round | 16/08/2008 | Lokomotiv Plovdiv | - | PSFC Chernomorets | 1:1 | ||||
| 5. Round | 13/09/2008 | PSFC Chernomorets | - | Lokomotiv Sofia | 1:1 | ||||
| 7. Round | 27/09/2008 | PSFC Chernomorets | - | Lokomotiv 2012 Mezdra | 2:2 | ||||
| 11. Round | 31/10/2008 | PSFC Chernomorets | - | Spartak Varna | 2:0 |  |
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| 12. Round | 10/11/2008 | Slavia Sofia | - | PSFC Chernomorets | 2:0 | ||||
| 16. Round | 07/03/2009 | PSFC Chernomorets | - | Botev Plovdiv | 2:1 | ||||
| 17. Round | 15/03/2009 | PSFC Chernomorets | - | Lokomotiv Plovdiv | 1:3 | ||||
| 21. Round | 12/04/2009 | PSFC Chernomorets | - | PFC Litex Lovech | 3:1 | |
Bulgaria