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GMT 01:00
| 26.05.1999 | |||
| 16:00 | Cibalia Vinkovci | 1-1 | HNK Zadar |
| 16:00 | Croatia Zagreb | 2-0 | NK Varaždin |
| 16:00 | HNK Rijeka | 1-1 | NK Osijek |
| 16:00 | Hrvatski Dragovoljac | 3-1 | Hajduk Split |
| 16:00 | Šibenik | 1-1 | Slaven Belupo |
| 16:00 | Suhopolje | 2-1 | NK Zagreb |
| 23.05.1999 | |||
| 16:00 | Hajduk Split | 1-3 | HNK Rijeka |
| 16:00 | HNK Zadar | 3-1 | Šibenik |
| 16:00 | NK Osijek | 0-1 | Croatia Zagreb |
| 16:00 | NK Varaždin | 3-2 | Hrvatski Dragovoljac |
| 16:00 | NK Zagreb | 3-1 | Cibalia Vinkovci |
| 16:00 | Slaven Belupo | 4-0 | Suhopolje |
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