1. Round | 09/08/2008 | OFC Sliven | - | Lokomotiv Plovdiv | 1:1 | ![]() |
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2. Round | 15/08/2008 | OFC Sliven | - | CSKA Sofia | 3:1 | ||||
3. Round | 23/08/2008 | Spartak Varna | - | OFC Sliven | 2:2 | ||||
4. Round | 30/08/2008 | OFC Sliven | - | Slavia Sofia | 1:1 | ||||
5. Round | 13/09/2008 | Minyor Pernik | - | OFC Sliven | 0:2 | ||||
9. Round | 20/10/2008 | PSFC Chernomorets | - | OFC Sliven | 1:1 | ||||
10. Round | 26/10/2008 | OFC Sliven | - | Levski Sofia | 0:0 | ![]() |
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13. Round | 15/11/2008 | PFC Litex Lovech | - | OFC Sliven | 2:0 | ||||
17. Round | 14/03/2009 | CSKA Sofia | - | OFC Sliven | 3:0 | ||||
18. Round | 18/03/2009 | OFC Sliven | - | Spartak Varna | 0:1 | ||||
21. Round | 12/04/2009 | Pirin Blagoevgrad | - | OFC Sliven | 3:1 | ||||
28. Round | 23/05/2009 | OFC Sliven | - | PFC Litex Lovech | 2:2 | ![]() |