Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 31.07.1999 |  | Matchday 2 | NK Osijek - Istra Pula | NK - IST | 1:0 | 2.500 |
| 07.09.1999 | | Matchday 4 | NK Osijek - NK Zagreb | NK - NK | 0:0 | 200 |
| 25.09.1999 | | Matchday 7 | NK Osijek - Hrvatski Dragovoljac | NK - | 2:1 | 1.500 |
| 30.09.1999 |  | 1. Round 2nd leg | NK Osijek - West Ham | NK - WHU | 1:3 | 15.000 |
| 12.10.1999 | | Matchday 9 | NK Osijek - Din. Zagreb | NK - DZG | 1:3 | 4.000 |
| 23.10.1999 | | Matchday 11 | NK Osijek - HNK Šibenik | NK - HNK | 3:0 | 500 |
| 30.10.1999 | | Matchday 12 | NK Osijek - HNK Rijeka | NK - RIJ | 3:2 | 1.000 |
| 23.11.1999 | | Matchday 14 | NK Osijek - Vukovar | NK - Vuk | 2:1 | 400 |
| 04.12.1999 | | Matchday 16 | NK Osijek - Slaven | NK - Sla | 2:1 | 500 |