14th March 2004
| Final | Livingston | 2-0 | Hibernian |
5th February 2004
| Semi Final | Hibernian | 1-1 | Rangers |
3rd February 2004
| Semi Final | Dundee | 0-1 | Livingston |
18th December 2003
| 4th Round | Hibernian | 2-1 | Celtic |
4th December 2003
| 3rd Round | Partick Thistle | 0-2 | Celtic |
3rd December 2003
| 4th Round | Rangers | 3-0 | St. Johnstone |
| 4th Round | Dundee | 1-0 | Heart of Midlothian |
2nd December 2003
| 4th Round | Aberdeen | 2-3 | Livingston |
29th October 2003
| 3rd Round | Dundee United | 0-1 | Livingston |
| 3rd Round | Clyde | 2-5 | Dundee |
| 3rd Round | Heart of Midlothian | 2-1 | Falkirk |
28th October 2003
| 3rd Round | Aberdeen | 5-0 | Brechin City |
| 3rd Round | St. Johnstone | 3-2 | Dunfermline Athletic |
| 3rd Round | Rangers | 6-0 | Forfar Athletic |
| 3rd Round | Hibernian | 2-1 | Queen of the South |
24th September 2003
| 2nd Round | Peterhead | 2-2 | Partick Thistle |
| 2nd Round | Dunfermline Athletic | 2-0 | Cowdenbeath |
23rd September 2003
| 2nd Round | Clyde | 2-1 | Airdrie United |
| 2nd Round | Dundee United | 3-1 | Greenock Morton |
| 2nd Round | Forfar Athletic | 3-3 | Motherwell |
| 2nd Round | Hibernian | 9-0 | Montrose |
| 2nd Round | Queen's Park | 1-3 | Livingston |
| 2nd Round | Ross County | 0-3 | Queen of the South |
| 2nd Round | St. Johnstone | 3-2 |
| 2nd Round | Aberdeen | 3-1 | Dumbarton |
| 2nd Round | Arbroath | 3-4 | Falkirk |
| 2nd Round | Brechin City | 1-0 | Kilmarnock |
3rd September 2003
| 1st Round | Greenock Morton | 2-0 | Stranraer |
2nd September 2003
| 1st Round | Montrose | 2-0 | Stirling Albion |
| 1st Round | 1-2 | Peterhead |
| 1st Round | Forfar Athletic | 1-0 |
| 1st Round | Elgin City | 0-4 | Brechin City |
| 1st Round | 1-2 | Ross County |
| 1st Round | East Fife | 0-2 | Airdrie United |
| 1st Round | Cowdenbeath | 3-0 | Alloa Athletic |
| 1st Round | Ayr United | 1-2 | Dumbarton |
| 1st Round | Stenhousemuir | 1-2 | Queen of the South |
| 1st Round | Inverness Caledonian Thistle | 1-2 | Queen's Park |
| 1st Round | 3-2 | Albion Rovers |
| 1st Round | St. Mirren | 0-2 | St. Johnstone |
| 1st Round | Arbroath | 1-0 | Raith Rovers |