| Tuesday 2nd September 2003 | |||
| First Round | |||
| Arbroath | 1-0 | Raith Rovers | |
| Ayr United | 1-2 | Dumbarton | |
| Cowdenbeath | 3-0 | Alloa Athletic | |
| East Fife | 0-2 | Airdrie United | |
| East Stirlingshire | 1-2 | Ross County | |
| Elgin City | 0-4 | Brechin City | |
| Forfar Athletic | 1-0 | Berwick Rangers | |
| Gretna | 1-2 | Peterhead | |
| Hamilton Academical | 3-2 | Albion Rovers | |
| Inverness CT | 1-2 | Queen's Park | |
| Montrose | 2-0 | Stirling Albion | |
| St Mirren | 0-2 | St Johnstone | aet |
| Stenhousemuir | 1-2 | Queen of the South | |
» Scottish League Cup 2003-2004 : Results
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