| Tuesday 5th August 2008 | |||
| First Round | |||
| Albion Rovers | 0-0 | Raith Rovers | aet |
| (Raith Rovers won on penalties) | |||
| Alloa Athletic | 2-0 | Elgin City | |
| Clyde | 4-1 | Queen's Park | |
| Dumbarton | 1-1 | Annan Athletic | aet |
| (Dumbarton won on penalties) | |||
| Montrose | 0-2 | Cowdenbeath | |
| Partick Thistle | 4-3 | Forfar Athletic | aet |
| Peterhead | 0-2 | Dunfermline Athletic | |
| Ross County | 2-3 | Airdrie United | aet |
| Stenhousemuir | 1-5 | St Johnstone | |
| Stranraer | 3-6 | Morton | |
» Scottish League Cup 2008-2009 : Results
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