| Tuesday 23rd September 2003 | |||
| Aberdeen | 3-1 | Dumbarton | |
| Arbroath | 3-4 | Falkirk | aet |
| Brechin City | 1-0 | Kilmarnock | |
| Clyde | 2-1 | Airdrie United | |
| Dundee United | 3-1 | Morton | |
| Forfar Athletic | 3-3 | Motherwell | aet |
| (Forfar Athletic won on penalties) | |||
| Hibernian | 9-0 | Montrose | |
| Queen's Park | 1-3 | Livingston | |
| Ross County | 0-3 | Queen of the South | |
| St Johnstone | 3-2 | Hamilton Academical | aet |
| Wednesday 24th September 2003 | |||
| Dunfermline Athletic | 2-0 | Cowdenbeath | |
| Peterhead | 2-2 | Partick Thistle | aet |
| (Partick Thistle won on penalties) | |||










