| 1. Jornada | 31.07.1999 | Dundee United | - | Dundee FC | 2:1 | ||||
| 3. Jornada | 14.08.1999 | Aberdeen FC | - | Dundee FC | 0:2 | ||||
| 4. Jornada | 21.08.1999 | Dundee FC | - | Celtic FC | 1:2 | ||||
| 5. Jornada | 28.08.1999 | Motherwell FC | - | Dundee FC | 0:2 | ||||
| 7. Jornada | 19.09.1999 | Dundee FC | - | St. Johnstone FC | 1:2 |  |
Inglaterra