| 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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| 15. Round | 31/10/2008 | FC Koper | - | NK Drava (old) | 3:1 | |
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| 21. Round | 21/02/2009 | NK Maribor | - | NK Drava (old) | 2:1 | |
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| 31. Round | 02/05/2009 | ND Gorica | - | NK Drava (old) | 3:5 | |
Slovenia