| 5. Ronde | 30.08.2008 | Airdrie United FC | - | Greenock Morton FC | 5:0 |  |
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| 11. Ronde | 04.11.2008 | Airdrie United FC | - | Dunfermline Athletic | 1:3 | |
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| 22. Ronde | 24.01.2009 | Airdrie United FC | - | Dundee FC | 1:0 | |
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| 25. Ronde | 22.02.2009 | Airdrie United FC | - | Clyde FC | 1:0 | |
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| 27. Ronde | 07.03.2009 | Airdrie United FC | - | Livingston FC | 4:4 | |
Schotland