| 3. Ronde | 16.08.2008 | Clyde FC | - | Ross County FC | 2:2 |  |
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| 5. Ronde | 30.08.2008 | Partick Thistle | - | Ross County FC | 0:1 | |
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| 7. Ronde | 20.09.2008 | Dunfermline Athletic | - | Ross County FC | 3:1 | |
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| 8. Ronde | 27.09.2008 | Ross County FC | - | Airdrie United FC | 2:0 | |
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| 9. Ronde | 04.10.2008 | Ross County FC | - | Greenock Morton FC | 3:0 | |
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| 10. Ronde | 18.10.2008 | Dundee FC | - | Ross County FC | 1:2 | |
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| 20. Ronde | 07.02.2009 | Ross County FC | - | St. Johnstone FC | 2:2 | |
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| 33. Ronde | 18.04.2009 | Ross County FC | - | Dunfermline Athletic | 1:3 | |
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| 35. Ronde | 02.05.2009 | Ross County FC | - | Livingston FC | 2:2 | |
Engeland