1. Round | 17/08/2009 | Dundee United | - | Heart of Midlothian | 2:0 | ||||
2. Round | 22/08/2009 | St. Mirren FC | - | Dundee United | 0:0 | ||||
3. Round | 29/08/2009 | Dundee United | - | Falkirk FC | 2:1 | ||||
5. Round | 19/09/2009 | Dundee United | - | Motherwell FC | 0:1 | ||||
8. Round | 17/10/2009 | Dundee United | - | Hamilton Academical | 1:1 | ||||
15. Round | 12/12/2009 | Heart of Midlothian | - | Dundee United | 0:0 | ||||
24. Round | 10/02/2010 | Dundee United | - | Hamilton Academical | 0:2 | ||||
31. Round | 27/03/2010 | Dundee United | - | Motherwell FC | 3:0 | ||||
30. Round | 31/03/2010 | Hibernian FC | - | Dundee United | 2:4 |