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| 1st(1st leg) | NK Pomorac | - | HNK Cibalia | 1:1 | ||
| 2nd (2nd leg) | HNK Cibalia | - | NK Pomorac | 4:2 pso | ||
| 1st(1st leg): 12/11/2008 13:00 | 2nd (2nd leg): 26/11/2008 16:00 | Winner: HNK Cibalia | ||||
| 1st(1st leg) | NK Zagora Unešić | - | Dinamo Zagreb | 1:2 | ||
| 2nd (2nd leg) | Dinamo Zagreb | - | NK Zagora Unešić | 5:1 | ||
| 1st(1st leg): 12/11/2008 13:00 | 2nd (2nd leg): 10/12/2008 13:00 | Winner: Dinamo Zagreb | ||||
| 1st(1st leg) | HNK Rijeka | - | NK Zagreb | 2:2 | ||
| 2nd (2nd leg) | NK Zagreb | - | HNK Rijeka | 4:2 pso | ||
| 1st(1st leg): 12/11/2008 16:00 | 2nd (2nd leg): 26/11/2008 16:00 | Winner: NK Zagreb | ||||
| 1st(1st leg) | Hajduk Split | - | Slaven Belupo | 0:0 | ||
| 2nd (2nd leg) | Slaven Belupo | - | Hajduk Split | 6:7 pso | ||
| 1st(1st leg): 12/11/2008 16:00 | 2nd (2nd leg): 26/11/2008 16:00 | Winner: Hajduk Split | ||||
