| 16. Round | 08/03/2009 | Cherno More Varna | - | Pirin Blagoevgrad | 1:0 | ||||
| 17. Round | 15/03/2009 | Vihren Sandanski | - | Cherno More Varna | 0:2 |  |
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| 18. Round | 18/03/2009 | Cherno More Varna | - | Botev Plovdiv | 1:0 | ||||
| 20. Round | 04/04/2009 | Cherno More Varna | - | Levski Sofia | 0:0 | ||||
| 21. Round | 13/04/2009 | Cherno More Varna | - | Lokomotiv Plovdiv | 2:1 | ||||
| 23. Round | 22/04/2009 | Cherno More Varna | - | PFC Litex Lovech | 0:0 | ||||
| 24. Round | 27/04/2009 | Lokomotiv 2012 Mezdra | - | Cherno More Varna | 1:3 | ||||
| 25. Round | 01/05/2009 | Cherno More Varna | - | Belasitsa Petrich | 6:0 |  |
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| 26. Round | 10/05/2009 | OFC Sliven | - | Cherno More Varna | 0:1 | |
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| 27. Round | 16/05/2009 | Cherno More Varna | - | CSKA Sofia | 1:0 | ||||
| 28. Round | 23/05/2009 | Spartak Varna | - | Cherno More Varna | 0:1 | |
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| 29. Round | 31/05/2009 | Cherno More Varna | - | Slavia Sofia | 2:0 |
Bulgaria