| 1. Round | 24/07/1999 | NK Vukovar 91 | - | NK Zagreb | 3:4 | ||||
| 4. Round | 07/09/1999 | Hrvatski Dragovoljac | - | NK Vukovar 91 | 1:1 | ||||
| 5. Round | 11/09/1999 | NK Vukovar 91 | - | Hajduk Split | 0:2 | ||||
| 6. Round | 17/09/1999 | Croatia Zagreb | - | NK Vukovar 91 | 5:0 | ||||
| 7. Round | 25/09/1999 | NK Vukovar 91 | - | NK Varteks | 2:2 | ||||
| 8. Round | 02/10/1999 | HNK Šibenik | - | NK Vukovar 91 | 2:1 | ||||
| 9. Round | 12/10/1999 | NK Vukovar 91 | - | HNK Rijeka | 0:0 | ||||
| 31. Round | 06/05/2000 | NK Vukovar 91 | - | HNK Šibenik | 2:1 | ||||
| 32. Round | 09/05/2000 | HNK Cibalia | - | NK Vukovar 91 | 5:2 | ||||
| 33. Round | 13/05/2000 | NK Vukovar 91 | - | NK Zagreb | 1:1 |
Croatia