| Saturday 23rd July 2011 | |||
| First Round | |||
| Airdrie United | 0-5 | Livingston | |
| Albion Rovers | 0-2 | Annan Athletic | |
| Arbroath | 1-2 | Dundee | aet |
| Ayr United | 2-0 | Queen of the South | aet |
| Brechin City | 1-2 | Falkirk | |
| Clyde | 2-2 | Berwick Rangers | aet |
| (Berwick Rangers won on penalties) | |||
| Deveronvale | 1-3 | Stirling Albion | |
| Forfar Athletic | 1-1 | Buckie Thistle | aet |
| (Forfar Athletic won on penalties) | |||
| Montrose | 1-6 | East Fife | |
| Partick Thistle | 2-1 | Stenhousemuir | |
| Peterhead | 2-2 | Alloa Athletic | aet |
| (Peterhead won on penalties) | |||
| Queen's Park | 0-2 | Hamilton Academical | |
| Raith Rovers | 2-1 | Cowdenbeath | |
| Ross County | 1-2 | Elgin City | |
| Stranraer | 0-8 | Morton | |
» Scottish Challenge Cup 2011-2012 : Results
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