| Tuesday 14th August 2007 | |||
| First Round | |||
| Albion Rovers | 1-1 | Berwick Rangers | aet |
| (Berwick Rangers won on penalties) | |||
| Clyde | 1-0 | Queen of the South | |
| Dundee | 1-2 | Ross County | |
| East Stirlingshire | 4-2 | Dumbarton | |
| Elgin City | 1-4 | Brechin City | |
| Forfar Athletic | 3-2 | East Fife | |
| Hamilton Academical | 1-2 | Ayr United | |
| Montrose | 5-1 | Stirling Albion | |
| Morton | 1-0 | Livingston | |
| Peterhead | 1-0 | Cowdenbeath | |
| Queen's Park | 1-0 | Stranraer | |
| Raith Rovers | 1-1 | St Johnstone | aet |
| (St Johnstone won on penalties) | |||
| Stenhousemuir | 1-3 | Airdrie United | |
» Scottish Challenge Cup 2007-2008 : Results
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