| 1. Round | 24/07/1999 | NK Istra Pula | - | Slaven Belupo | 0:2 |  |
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| 2. Round | 31/07/1999 | Slaven Belupo | - | NK Vukovar 91 | 1:2 |  |
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| 4. Round | 07/09/1999 | HNK Cibalia | - | Slaven Belupo | 0:0 | ||||
| 5. Round | 11/09/1999 | Slaven Belupo | - | NK Osijek | 1:4 | ||||
| 8. Round | 02/10/1999 | Croatia Zagreb | - | Slaven Belupo | 5:1 | |
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| 9. Round | 12/10/1999 | Slaven Belupo | - | NK Varteks | 2:1 | ||||
| 10. Round | 16/10/1999 | HNK Šibenik | - | Slaven Belupo | 0:0 | |
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| 12. Round | 30/10/1999 | Slaven Belupo | - | NK Istra Pula | 1:1 | ||||
| 15. Round | 27/11/1999 | Slaven Belupo | - | HNK Cibalia | 1:0 | ||||
| 17. Round | 19/02/2000 | Slaven Belupo | - | Hrvatski Dragovoljac | 0:1 | ||||
| 18. Round | 26/02/2000 | Hajduk Split | - | Slaven Belupo | 1:0 | ||||
| 19. Round | 29/02/2000 | Slaven Belupo | - | Croatia Zagreb | 0:5 | ||||
| 20. Round | 04/03/2000 | NK Varteks | - | Slaven Belupo | 0:1 | ||||
| 21. Round | 07/03/2000 | Slaven Belupo | - | HNK Šibenik | 0:0 | ||||
| 22. Round | 11/03/2000 | HNK Rijeka | - | Slaven Belupo | 1:1 |
Croatia