| 20. Ronde | 03.01.2009 | Greenock Morton FC | - | Queen Of The South | 2:2 |  |
|||
| 25. Ronde | 21.02.2009 | Queen Of The South | - | St. Johnstone FC | 3:3 | |
|||
| 28. Ronde | 10.03.2009 | Dundee FC | - | Queen Of The South | 2:3 | |
|||
| 30. Ronde | 21.03.2009 | Queen Of The South | - | Livingston FC | 3:3 | |
Schotland