| 2. Round | 15/08/2009 | Minyor Pernik | - | Levski Sofia | 0:2 | ||||
| 4. Round | 29/08/2009 | Slavia Sofia | - | Levski Sofia | 1:3 |  |
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| 5. Round | 12/09/2009 | Levski Sofia | - | Lokomotiv Sofia | 1:2 | ||||
| 7. Round | 27/09/2009 | Levski Sofia | - | PSFC Chernomorets | 0:1 | |
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| 8. Round | 04/10/2009 | Lokomotiv Plovdiv | - | Levski Sofia | 2:2 | ||||
| 9. Round | 18/10/2009 | Levski Sofia | - | PFC Beroe | 0:1 | ||||
| 13. Round | 21/11/2009 | Levski Sofia | - | Cherno More Varna | 3:0 | ||||
| 3. Round | 25/11/2009 | Levski Sofia | - | PFC Litex Lovech | 2:2 | |
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| 14. Round | 28/11/2009 | Levski Sofia | - | PFC Montana | 3:1 |
Brazil