| 1. Ronde | 09.08.2008 | FC Pirin | - | Cherno More Varna | 1:2 | ||||
| 5. Ronde | 12.09.2008 | Levski Sofia | - | Cherno More Varna | 3:0 | ||||
| 6. Ronde | 21.09.2008 | Lokomotiv Plovdiv | - | Cherno More Varna | 1:0 | ||||
| 7. Ronde | 26.09.2008 | Cherno More Varna | - | Lokomotiv Sofia | 1:0 | ||||
| 8. Ronde | 06.10.2008 | PFC Litex Lovech | - | Cherno More Varna | 1:0 | ||||
| 9. Ronde | 19.10.2008 | Cherno More Varna | - | Lokomotiv 2012 Mezdra | 2:0 |  |
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| 10. Ronde | 26.10.2008 | Belasitsa Petrich | - | Cherno More Varna | 2:0 | ||||
| 13. Ronde | 14.11.2008 | Cherno More Varna | - | Spartak Varna | 5:0 | ||||
| 14. Ronde | 24.11.2008 | Slavia Sofia | - | Cherno More Varna | 0:2 | ||||
| 20. Ronde | 04.04.2009 | Cherno More Varna | - | Levski Sofia | 0:0 | ||||
| 21. Ronde | 13.04.2009 | Cherno More Varna | - | Lokomotiv Plovdiv | 2:1 | ||||
| 22. Ronde | 18.04.2009 | Lokomotiv Sofia | - | Cherno More Varna | 3:2 | ||||
| 23. Ronde | 22.04.2009 | Cherno More Varna | - | PFC Litex Lovech | 0:0 | ||||
| 29. Ronde | 31.05.2009 | Cherno More Varna | - | Slavia Sofia | 2:0 |
Bulgarije