| 1. Round | 24/07/1999 | HNK Rijeka | - | NK Osijek | 0:1 | ||||
| 2. Round | 31/07/1999 | NK Osijek | - | NK Istra Pula | 1:0 | ||||
| 3. Round | 28/08/1999 | NK Vukovar 91 | - | NK Osijek | 3:1 | ||||
| 4. Round | 07/09/1999 | NK Osijek | - | NK Zagreb | 0:0 | ||||
| 5. Round | 11/09/1999 | Slaven Belupo | - | NK Osijek | 1:4 |  |
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| 6. Round | 19/09/1999 | HNK Cibalia | - | NK Osijek | 2:3 | |
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| 7. Round | 25/09/1999 | NK Osijek | - | Hrvatski Dragovoljac | 2:1 | ||||
| 8. Round | 03/10/1999 | Hajduk Split | - | NK Osijek | 5:4 | |
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| 9. Round | 12/10/1999 | NK Osijek | - | Croatia Zagreb | 1:3 | ||||
| 10. Round | 16/10/1999 | NK Varteks | - | NK Osijek | 2:0 | ||||
| 11. Round | 23/10/1999 | NK Osijek | - | HNK Šibenik | 3:0 | ||||
| 12. Round | 30/10/1999 | NK Osijek | - | HNK Rijeka | 3:2 | ||||
| 13. Round | 06/11/1999 | NK Istra Pula | - | NK Osijek | 1:1 | |
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| 14. Round | 23/11/1999 | NK Osijek | - | NK Vukovar 91 | 2:1 | |
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| 16. Round | 04/12/1999 | NK Osijek | - | Slaven Belupo | 2:1 |
Croatia