Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 24.07.1999 |  | Matchday 1 | HNK Šibenik - Hrvatski Dragovoljac | HNK - | 0:0 | 2.000 |
| 29.08.1999 | | Matchday 3 | HNK Šibenik - Din. Zagreb | HNK - DZG | 1:1 | 6.000 |
| 11.09.1999 | | Matchday 5 | HNK Šibenik - HNK Cibalia | HNK - Cib | 2:2 | 800 |
| 18.09.1999 | | Matchday 6 | HNK Šibenik - HNK Rijeka | HNK - RIJ | 0:2 | 1.000 |
| 02.10.1999 | | Matchday 8 | HNK Šibenik - Vukovar | HNK - Vuk | 2:1 | 800 |
| 16.10.1999 | | Matchday 10 | HNK Šibenik - Slaven | HNK - Sla | 0:0 | 500 |
| 06.11.1999 | | Matchday 13 | HNK Šibenik - Hajduk | HNK - HAJ | 1:3 | 4.000 |
| 27.11.1999 | | Matchday 15 | HNK Šibenik - NK Varaždin | HNK - VAR | 2:0 | 800 |