1. Round | 10/08/2008 | Botev Plovdiv | - | PSFC Chernomorets | 0:1 | ||||
2. Round | 16/08/2008 | Lokomotiv Plovdiv | - | PSFC Chernomorets | 1:1 | ||||
4. Round | 31/08/2008 | Cherno More Varna | - | PSFC Chernomorets | 0:1 | ||||
6. Round | 21/09/2008 | PFC Litex Lovech | - | PSFC Chernomorets | 2:2 | ||||
7. Round | 27/09/2008 | PSFC Chernomorets | - | Lokomotiv 2012 Mezdra | 2:2 | ||||
8. Round | 04/10/2008 | Belasitsa Petrich | - | PSFC Chernomorets | 0:1 | ||||
14. Round | 23/11/2008 | FC Pirin | - | PSFC Chernomorets | 2:1 |