1. Round | 24/07/1999 | NK Istra Pula | - | Slaven Belupo | 0:2 | ||||
2. Round | 31/07/1999 | NK Osijek | - | NK Istra Pula | 1:0 | ||||
4. Round | 07/09/1999 | Hajduk Split | - | NK Istra Pula | 1:0 | ||||
5. Round | 10/09/1999 | NK Istra Pula | - | Croatia Zagreb | 0:4 | ||||
7. Round | 25/09/1999 | NK Istra Pula | - | HNK Šibenik | 0:0 |