| 5. Ronde | 30.08.2008 | Airdrie United FC | - | Greenock Morton FC | 5:0 |  |
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| 6. Ronde | 13.09.2008 | Livingston FC | - | Airdrie United FC | 1:2 | |
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| 10. Ronde | 18.10.2008 | Airdrie United FC | - | Queen Of The South | 2:0 | |
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| 12. Ronde | 01.11.2008 | Dundee FC | - | Airdrie United FC | 1:1 | |
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| 17. Ronde | 13.12.2008 | Partick Thistle | - | Airdrie United FC | 2:1 | |
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| 19. Ronde | 27.12.2008 | Airdrie United FC | - | Greenock Morton FC | 1:0 | |
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| 20. Ronde | 03.01.2009 | Livingston FC | - | Airdrie United FC | 1:1 | |
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| 21. Ronde | 17.01.2009 | Dunfermline Athletic | - | Airdrie United FC | 1:1 | |
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| 32. Ronde | 11.04.2009 | Dundee FC | - | Airdrie United FC | 0:1 | |
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| 35. Ronde | 02.05.2009 | Partick Thistle | - | Airdrie United FC | 0:1 | |
Canada