| 8. Round | 03/10/1999 | Hajduk Split | - | NK Osijek | 5:4 | ||||
| 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 | ||||
| 15. Round | 27/11/1999 | NK Zagreb | - | NK Osijek | 2:1 | ||||
| 17. Round | 19/02/2000 | NK Osijek | - | HNK Cibalia | 1:1 | |
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| 19. Round | 29/02/2000 | NK Osijek | - | Hajduk Split | 2:0 | ||||
| 20. Round | 04/03/2000 | Croatia Zagreb | - | NK Osijek | 3:1 | ||||
| 21. Round | 07/03/2000 | NK Osijek | - | NK Varteks | 1:1 | ||||
| 24. Round | 25/03/2000 | NK Vukovar 91 | - | NK Osijek | 1:1 | ||||
| 25. Round | 01/04/2000 | NK Osijek | - | NK Istra Pula | 3:1 | |
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| 26. Round | 08/04/2000 | HNK Šibenik | - | NK Osijek | 1:1 | ||||
| 28. Round | 15/04/2000 | NK Zagreb | - | NK Osijek | 2:2 | ||||
| 29. Round | 24/04/2000 | NK Osijek | - | HNK Rijeka | 2:0 | ||||
| 30. Round | 29/04/2000 | NK Osijek | - | NK Varteks | 0:0 | ||||
| 31. Round | 06/05/2000 | Hajduk Split | - | NK Osijek | 1:0 | ||||
| 33. Round | 13/05/2000 | Slaven Belupo | - | NK Osijek | 5:2 |
Croatia