| Saturday 24th July 2010 | |||
| First Round | |||
| Airdrie United | 1-2 | Ayr United | |
| Dundee | 2-1 | Alloa Athletic | |
| Dunfermline Athletic | 1-0 | Arbroath | |
| East Fife | 4-3 | Brechin City | aet |
| Elgin City | 1-2 | Ross County | |
| Partick Thistle | 2-1 | Clyde | |
| Peterhead | 5-0 | Montrose | |
| Queen of the South | 2-1 | Albion Rovers | |
| Queen's Park | 3-2 | Livingston | aet |
| Raith Rovers | 0-1 | Cowdenbeath | |
| Stenhousemuir | 3-2 | Annan Athletic | |
| Stirling Albion | 0-0 | Falkirk | aet |
| (Stirling Albion won on penalties) | |||
| Stranraer | 1-2 | East Stirlingshire | aet |
» Scottish Challenge Cup 2010-2011 : Results
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