| 3. Round | 02/08/2008 | NK Maribor | - | NK Drava (old) | 1:1 |  |
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| 4. Round | 10/08/2008 | NK Drava (old) | - | ND Gorica | 5:1 | |
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| 5. Round | 17/08/2008 | Interblock Ljubljana | - | NK Drava (old) | 1:2 | |
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| 28. Round | 11/04/2009 | NK Drava (old) | - | NK Nafta | 4:1 | ||||
| 31. Round | 02/05/2009 | ND Gorica | - | NK Drava (old) | 3:5 | |
Slovenia