| 1. Round | 08/08/2009 | Queen Of The South | - | Raith Rovers | 1:1 |  |
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| 5. Round | 12/09/2009 | Ross County FC | - | Queen Of The South | 3:2 | |
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| 6. Round | 19/09/2009 | Queen Of The South | - | Dundee FC | 2:0 | |
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| 7. Round | 26/09/2009 | Dunfermline Athletic | - | Queen Of The South | 1:4 | |
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| 9. Round | 10/10/2009 | Inverness CT | - | Queen Of The South | 1:3 | |
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| 13. Round | 07/11/2009 | Ayr United | - | Queen Of The South | 0:1 | |
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| 17. Round | 12/12/2009 | Greenock Morton FC | - | Queen Of The South | 1:2 | |
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| 25. Round | 09/03/2010 | Inverness CT | - | Queen Of The South | 3:1 | |
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| 18. Round | 17/04/2010 | Queen Of The South | - | Raith Rovers | 3:0 | |
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| 35. Round | 24/04/2010 | Queen Of The South | - | Airdrie United FC | 2:2 | |
Scotland