| 1. Round | 24/07/1999 | NK Vukovar 91 | - | NK Zagreb | 3:4 | ||||
| 2. Round | 31/07/1999 | Slaven Belupo | - | NK Vukovar 91 | 1:2 | ||||
| 3. Round | 28/08/1999 | NK Vukovar 91 | - | NK Osijek | 3:1 | ||||
| 5. Round | 11/09/1999 | NK Vukovar 91 | - | Hajduk Split | 0:2 | ||||
| 8. Round | 02/10/1999 | HNK Šibenik | - | NK Vukovar 91 | 2:1 | ||||
| 9. Round | 12/10/1999 | NK Vukovar 91 | - | HNK Rijeka | 0:0 | ||||
| 10. Round | 16/10/1999 | NK Istra Pula | - | NK Vukovar 91 | 3:0 | ||||
| 11. Round | 23/10/1999 | NK Vukovar 91 | - | HNK Cibalia | 0:0 |  |
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| 13. Round | 06/11/1999 | NK Vukovar 91 | - | Slaven Belupo | 0:0 |
Croatia