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| U | NK Pomorac | - | HNK Cibalia | 1:1 | ||
| R | HNK Cibalia | - | NK Pomorac | 4:2 d.p. | ||
| U: 12.11.2008 14:00 | R: 26.11.2008 17:00 | Winnaars: HNK Cibalia | ||||
| U | NK Zagora Unešić | - | Dinamo Zagreb | 1:2 | ||
| R | Dinamo Zagreb | - | NK Zagora Unešić | 5:1 | ||
| U: 12.11.2008 14:00 | R: 10.12.2008 14:00 | Winnaars: Dinamo Zagreb | ||||
| U | HNK Rijeka | - | NK Zagreb | 2:2 | ||
| R | NK Zagreb | - | HNK Rijeka | 4:2 d.p. | ||
| U: 12.11.2008 17:00 | R: 26.11.2008 17:00 | Winnaars: NK Zagreb | ||||
| U | Hajduk Split | - | Slaven Belupo | 0:0 | ||
| R | Slaven Belupo | - | Hajduk Split | 6:7 d.p. | ||
| U: 12.11.2008 17:00 | R: 26.11.2008 17:00 | Winnaars: Hajduk Split | ||||
