| 2. Round | 10/08/2002 | Dundee United | - | Kilmarnock FC | 1:2 | ||||
| 3. Round | 17/08/2002 | Celtic FC | - | Dundee United | 5:0 | ||||
| 4. Round | 25/08/2002 | Dundee United | - | Motherwell FC | 1:1 | ||||
| 5. Round | 31/08/2002 | Dundee United | - | Dundee FC | 0:0 |  |
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| 8. Round | 21/09/2002 | Heart of Midlothian | - | Dundee United | 2:0 | ||||
| 13. Round | 02/11/2002 | Kilmarnock FC | - | Dundee United | 1:2 | ||||
| 14. Round | 10/11/2002 | Dundee United | - | Celtic FC | 0:2 | ||||
| 16. Round | 23/11/2002 | Dundee FC | - | Dundee United | 3:2 | ||||
| 18. Round | 04/12/2002 | Dunfermline Athletic | - | Dundee United | 4:1 | ||||
| 20. Round | 14/12/2002 | Rangers FC | - | Dundee United | 3:0 | ||||
| 21. Round | 21/12/2002 | Dundee United | - | Heart of Midlothian | 0:3 | ||||
| 26. Round | 01/02/2003 | Dundee United | - | Motherwell FC | 2:1 | ||||
| 27. Round | 09/02/2003 | Dundee United | - | Dundee FC | 1:1 | ||||
| 28. Round | 16/02/2003 | Aberdeen FC | - | Dundee United | 3:0 | ||||
| 29. Round | 01/03/2003 | Dundee United | - | Dunfermline Athletic | 3:0 | ||||
| 32. Round | 05/04/2003 | Heart of Midlothian | - | Dundee United | 2:1 | ||||
| 33. Round | 13/04/2003 | Dundee United | - | Rangers FC | 1:4 |
Scotland