| 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 | ||||
| 5. Round | 13/09/2008 | PSFC Chernomorets | - | Lokomotiv Sofia | 1:1 | ||||
| 7. Round | 27/09/2008 | PSFC Chernomorets | - | Lokomotiv 2012 Mezdra | 2:2 |  |
|||
| 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 | ||||
| 3. Round | 05/11/2008 | PSFC Chernomorets | - | Levski Sofia | 2:2 | ||||
| 12. Round | 10/11/2008 | Slavia Sofia | - | PSFC Chernomorets | 2:0 | ||||
| 13. Round | 17/11/2008 | PSFC Chernomorets | - | Minyor Pernik | 1:1 | ||||
| 14. Round | 23/11/2008 | FC Pirin | - | PSFC Chernomorets | 2:1 | ||||
| 15. Round | 29/11/2008 | PSFC Chernomorets | - | Vihren Sandanski | 1:3 |
Nigeria