| 20. Round | 04/04/2009 | Lokomotiv Sofia | - | PSFC Chernomorets | 2:0 | ||||
| 21. Round | 12/04/2009 | PSFC Chernomorets | - | PFC Litex Lovech | 3:1 | ||||
| 22. Round | 20/04/2009 | Lokomotiv 2012 Mezdra | - | PSFC Chernomorets | 1:1 | ||||
| 23. Round | 23/04/2009 | PSFC Chernomorets | - | Belasitsa Petrich | 2:0 | ||||
| 24. Round | 27/04/2009 | OFC Sliven | - | PSFC Chernomorets | 0:0 | ||||
| 25. Round | 02/05/2009 | PSFC Chernomorets | - | CSKA Sofia | 0:1 | ||||
| 26. Round | 09/05/2009 | Spartak Varna | - | PSFC Chernomorets | 0:3 | ||||
| 27. Round | 16/05/2009 | PSFC Chernomorets | - | Slavia Sofia | 2:1 | ||||
| 28. Round | 23/05/2009 | Minyor Pernik | - | PSFC Chernomorets | 1:0 | ||||
| 29. Round | 31/05/2009 | PSFC Chernomorets | - | Pirin Blagoevgrad | 3:1 | ||||
| 30. Round | 13/06/2009 | Vihren Sandanski | - | PSFC Chernomorets | 3:5 |
Germany