| Saturday 26th July 2008 | |||
| First Round | |||
| Airdrie United | 3-2 | Dumbarton | |
| Alloa Athletic | 2-1 | Dundee | |
| Arbroath | 1-2 | Forfar Athletic | |
| Berwick Rangers | 1-5 | Queen of the South | |
| Brechin City | 0-1 | East Fife | |
| Clyde | 2-0 | Annan Athletic | |
| Dunfermline Athletic | 3-0 | Stirling Albion | |
| Elgin City | 0-2 | Cowdenbeath | |
| Livingston | 4-0 | Stranraer | |
| Partick Thistle | 2-1 | Queen's Park | |
| Peterhead | 6-0 | Montrose | |
| Ross County | 2-1 | St Johnstone | |
| Stenhousemuir | 0-1 | Albion Rovers | |
» Scottish Challenge Cup 2008-2009 : Results
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