Gameplan
| Date | Round | Match | Match | Res. | Attendance | |
|---|---|---|---|---|---|---|
| 02.01.1999 |  | Matchday 21 | Dundee FC - Dundee Utd | Dun - DUN | 1:3 | 11.751 |
| 27.01.1999 | | Matchday 16 | Dundee FC - Rangers FC | Dun - RAN | 0:4 | 9.453 |
| 06.02.1999 | | Matchday 23 | Dundee FC - Motherwell | Dun - MOT | 1:0 | 4.187 |
| 27.02.1999 | | Matchday 25 | Dundee FC - St. Johnstone | Dun - STJ | 0:1 | 7.245 |
| 20.03.1999 | | Matchday 28 | Dundee FC - Hearts FC | Dun - HEA | 2:0 | 6.612 |
| 18.04.1999 | | Matchday 31 | Dundee FC - Rangers FC | Dun - RAN | 1:1 | 11.051 |
| 24.04.1999 | | Matchday 32 | Dundee FC - Kilmarnock | Dun - KIL | 2:1 | 4.296 |
| 15.05.1999 | | Matchday 35 | Dundee FC - Dunfermline | Dun - DUN | 3:1 | 4.179 |
| 08.08.1999 | | Matchday 2 | Dundee FC - Hibernian FC | Dun - HIB | 3:4 | 6.050 |
| 21.08.1999 | | Matchday 4 | Dundee FC - Celtic | Dun - CEL | 1:2 | 10.531 |
| 19.09.1999 | | Matchday 7 | Dundee FC - St. Johnstone | Dun - STJ | 1:2 | 5.283 |
| 02.10.1999 | | Matchday 9 | Dundee FC - Rangers FC | Dun - RAN | 2:3 | 10.494 |
| 17.10.1999 | | Matchday 10 | Dundee FC - Dundee Utd | Dun - DUN | 0:2 | 9.484 |
| 30.10.1999 | | Matchday 12 | Dundee FC - Hearts FC | Dun - HEA | 1:0 | 6.018 |
| 20.11.1999 | | Matchday 14 | Dundee FC - Motherwell | Dun - MOT | 0:1 | 4.340 |
| 27.12.1999 | | Matchday 20 | Dundee FC - St. Johnstone | Dun - STJ | 1:1 | 6.232 |