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| Sunday, July 25, 2010 | ||||
| First Round South-West | ||||
| Dumbarton | 0 - 0 | Morton | Match reportMorton win 4-3 on penalties | |
| Half-time: 0 - 0 | ||||
| Saturday, July 24, 2010 | ||||
| First Round North-East | ||||
| Dundee | 2 - 1 | Alloa Athletic | Match report | |
| Half-time: 0 - 0 | ||||
| Dunfermline Athletic | 1 - 0 | Arbroath | Match report | |
| Half-time: 0 - 0 | ||||
| East Fife | 4 - 3 | Brechin City | Match reportAfter Extra Time | |
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Half-time: 0 - 1 Extra-time: 4 - 3 |
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| Elgin City | 1 - 2 | Ross County | Match report | |
| Half-time: 0 - 0 | ||||
| Peterhead | 5 - 0 | Montrose | Match report | |
| Half-time: 1 - 0 | ||||
| Raith Rovers | 0 - 1 | Cowdenbeath | Match report | |
| Half-time: 0 - 0 | ||||
| Stirling Albion | 0 - 0 | Falkirk | Match reportStirling win 3-1 on penalties | |
| Half-time: 0 - 0 | ||||
| First Round South-West | ||||
| Airdrie United | 1 - 2 | Ayr United | Match report | |
| Half-time: 0 - 0 | ||||
| Partick Thistle | 2 - 1 | Clyde | Match report | |
| Half-time: 1 - 1 | ||||
| Queen of the South | 2 - 1 | Albion Rovers | Match report | |
| Half-time: 1 - 0 | ||||
| Queen's Park | 3 - 2 | Livingston | Match reportAfter Extra Time | |
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Half-time: 1 - 1 Extra-time: 3 - 2 |
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| Stenhousemuir | 3 - 2 | Annan Athletic | Match report | |
| Half-time: 3 - 0 | ||||
| Stranraer | 1 - 2 | East Stirlingshire | Match reportAfter Extra Time | |
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Half-time: 0 - 0 Extra-time: 1 - 2 |
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