1. Round | 11/08/2008 | Hamilton Academical | - | Dundee United | 3:1 | ||||
2. Round | 17/08/2008 | Dundee United | - | Celtic FC | 1:1 | ||||
3. Round | 23/08/2008 | Motherwell FC | - | Dundee United | 1:1 | ||||
4. Round | 30/08/2008 | Dundee United | - | Kilmarnock FC | 0:2 | ||||
5. Round | 13/09/2008 | Hibernian FC | - | Dundee United | 2:1 | ||||
24. Round | 31/01/2009 | Rangers FC | - | Dundee United | 2:0 | ||||
26. Round | 21/02/2009 | Aberdeen FC | - | Dundee United | 2:2 | ||||
27. Round | 28/02/2009 | Dundee United | - | Heart of Midlothian | 0:1 |