1. Round | 02/05/2009 | Hibernian FC | - | Dundee United | 1:2 | ||||
2. Round | 07/05/2009 | Dundee United | - | Aberdeen FC | 1:1 | ||||
3. Round | 12/05/2009 | Celtic FC | - | Dundee United | 2:1 | ||||
4. Round | 16/05/2009 | Heart of Midlothian | - | Dundee United | 3:0 | ||||
5. Round | 24/05/2009 | Dundee United | - | Rangers FC | 0:3 |