1. Round | 24/07/1999 | NK Istra Pula | - | Slaven Belupo | 0:2 | ||||
8. Round | 02/10/1999 | HNK Rijeka | - | NK Istra Pula | 4:1 | ||||
9. Round | 12/10/1999 | NK Istra Pula | - | HNK Cibalia | 3:0 | ||||
12. Round | 30/10/1999 | Slaven Belupo | - | NK Istra Pula | 1:1 | ||||
14. Round | 23/11/1999 | Hrvatski Dragovoljac | - | NK Istra Pula | 1:0 | ||||
16. Round | 04/12/1999 | Croatia Zagreb | - | NK Istra Pula | 3:1 |