| 2. Ronde | 09.08.2008 | Livingston FC | - | Ross County FC | 2:0 |  |
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| 3. Ronde | 16.08.2008 | Greenock Morton FC | - | Livingston FC | 1:2 | |
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| 4. Ronde | 23.08.2008 | Livingston FC | - | Clyde FC | 2:1 | |
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| 5. Ronde | 30.08.2008 | Dunfermline Athletic | - | Livingston FC | 1:2 | |
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| 17. Ronde | 13.12.2008 | Ross County FC | - | Livingston FC | 1:4 | |
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| 22. Ronde | 24.01.2009 | Greenock Morton FC | - | Livingston FC | 2:2 | |
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| 23. Ronde | 31.01.2009 | Livingston FC | - | Ross County FC | 4:2 | |
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| 26. Ronde | 28.02.2009 | Livingston FC | - | Partick Thistle | 2:4 | |
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| 27. Ronde | 07.03.2009 | Airdrie United FC | - | Livingston FC | 4:4 | |
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| 29. Ronde | 14.03.2009 | Livingston FC | - | St. Johnstone FC | 1:0 | |
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| 30. Ronde | 21.03.2009 | Queen Of The South | - | Livingston FC | 3:3 | |
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| 35. Ronde | 02.05.2009 | Ross County FC | - | Livingston FC | 2:2 | |
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| 36. Ronde | 09.05.2009 | Livingston FC | - | Queen Of The South | 2:2 | |
Schotland
