| 1. Ronde | 02.08.2008 | Ross County FC | - | Dundee FC | 1:2 |  |
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| 2. Ronde | 09.08.2008 | Dundee FC | - | Clyde FC | 1:0 | |
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| 10. Ronde | 18.10.2008 | Dundee FC | - | Ross County FC | 1:2 | |
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| 12. Ronde | 01.11.2008 | Dundee FC | - | Airdrie United FC | 1:1 | |
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| 13. Ronde | 08.11.2008 | Dunfermline Athletic | - | Dundee FC | 0:1 | |
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| 15. Ronde | 29.11.2008 | Dundee FC | - | St. Johnstone FC | 1:1 | |
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| 23. Ronde | 31.01.2009 | Dundee FC | - | Clyde FC | 2:1 | |
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| 16. Ronde | 07.02.2009 | Livingston FC | - | Dundee FC | 1:2 | |
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| 25. Ronde | 21.02.2009 | Dundee FC | - | Livingston FC | 4:1 | |
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| 28. Ronde | 10.03.2009 | Dundee FC | - | Queen Of The South | 2:3 | |
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| 29. Ronde | 14.03.2009 | Dundee FC | - | Ross County FC | 2:0 | |
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| 24. Ronde | 28.03.2009 | Ross County FC | - | Dundee FC | 1:1 | |
Frankrijk
Guadeloupe