| 19. Ronde | 27.12.2008 | Queen Of The South | - | Dundee FC | 0:1 |  |
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| 23. Ronde | 31.01.2009 | Dundee FC | - | Clyde FC | 2:1 | |
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| 29. Ronde | 14.03.2009 | Dundee FC | - | Ross County FC | 2:0 | |
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| 30. Ronde | 22.03.2009 | Partick Thistle | - | Dundee FC | 1:1 | |
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| 36. Ronde | 09.05.2009 | Dundee FC | - | Partick Thistle | 4:0 | |
Schotland