| 1. Round | 24/07/1999 | NK Vukovar 91 | - | NK Zagreb | 3:4 | ||||
| 2. Round | 31/07/1999 | HNK Cibalia | - | NK Zagreb | 0:0 | ||||
| 3. Round | 28/08/1999 | NK Zagreb | - | Slaven Belupo | 0:1 | ||||
| 4. Round | 07/09/1999 | NK Osijek | - | NK Zagreb | 0:0 | ||||
| 5. Round | 11/09/1999 | NK Zagreb | - | Hrvatski Dragovoljac | 3:3 | ||||
| 12. Round | 30/10/1999 | NK Zagreb | - | NK Vukovar 91 | 1:0 | ||||
| 13. Round | 06/11/1999 | NK Zagreb | - | HNK Cibalia | 0:0 | ||||
| 14. Round | 23/11/1999 | Slaven Belupo | - | NK Zagreb | 1:1 | ||||
| 15. Round | 27/11/1999 | NK Zagreb | - | NK Osijek | 2:1 |
Romania