 |
 |
| 1. HNL | 31/07/1999 | NK Osijek | - | NK Istra Pula | 1:0 | 2.500 |
| 1. HNL | 07/09/1999 | NK Osijek | - | NK Zagreb | 0:0 | 200 |
| 1. HNL | 25/09/1999 | NK Osijek | - | Hrvatski Dragovoljac | 2:1 | 1.500 |
| EL | 30/09/1999 | NK Osijek | - | West Ham United | 1:3 | 15.000 |
| 1. HNL | 12/10/1999 | NK Osijek | - | Croatia Zagreb | 1:3 | 4.000 |
| 1. HNL | 23/10/1999 | NK Osijek | - | HNK Šibenik | 3:0 | 500 |
| 1. HNL | 30/10/1999 | NK Osijek | - | HNK Rijeka | 3:2 | 1.000 |
| 1. HNL | 23/11/1999 | NK Osijek | - | NK Vukovar 91 | 2:1 | 400 |
| 1. HNL | 04/12/1999 | NK Osijek | - | Slaven Belupo | 2:1 | 500 |
Croatia