| No matches in July 2009 - found first matches after that month | |||
| Saturday 1st August 2009 | |||
| First Round | |||
| Airdrie United | 0-0 | Alloa Athletic | aet |
| (Alloa Athletic won on penalties) | |||
| Albion Rovers | 3-0 | Livingston | |
| Brechin City | 4-0 | Elgin City | |
| Clyde | 1-3 | Forfar Athletic | |
| Cowdenbeath | 1-3 | Morton | |
| Dumbarton | 0-5 | Dunfermline Athletic | |
| Dundee | 5-0 | Stranraer | |
| East Fife | 2-3 | Raith Rovers | |
| Inverness CT | 4-0 | Annan Athletic | |
| Partick Thistle | 5-1 | Berwick Rangers | |
| Peterhead | 0-3 | Arbroath | |
| Queen's Park | 1-4 | Queen of the South | |
| Ross County | 5-0 | Montrose | |
| Stenhousemuir | 0-5 | St Johnstone | |
| Stirling Albion | 1-2 | Ayr United | aet |
» Scottish League Cup 2009-2010 : Results
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