| 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 | ||||
| 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 | ||||
| 8. Ronde | 04.10.2008 | Belasitsa Petrich | - | PSFC Chernomorets | 0:1 | ||||
| 9. Ronde | 20.10.2008 | PSFC Chernomorets | - | OFC Sliven | 1:1 | ||||
| 14. Ronde | 23.11.2008 | FC Pirin | - | PSFC Chernomorets | 2:1 | ||||
| 17. Ronde | 15.03.2009 | PSFC Chernomorets | - | Lokomotiv Plovdiv | 1:3 | ||||
| 18. Ronde | 18.03.2009 | Levski Sofia | - | PSFC Chernomorets | 3:1 | ||||
| 19. Ronde | 21.03.2009 | PSFC Chernomorets | - | Cherno More Varna | 0:0 | ||||
| 29. Ronde | 31.05.2009 | PSFC Chernomorets | - | Pirin Blagoevgrad | 3:1 |
Bulgarije