26th October 2003
| Final | Inverness Caledonian Thistle | 2-0 | Airdrie United |
17th September 2003
| Semi Final | Brechin City | 1-2 | Airdrie United |
16th September 2003
| Semi Final | Raith Rovers | 0-4 | Inverness Caledonian Thistle |
26th August 2003
| Quarter Final | Inverness Caledonian Thistle | 1-0 | Ross County |
| Quarter Final | Forfar Athletic | 0-2 | Airdrie United |
| Quarter Final | Raith Rovers | 3-2 | St. Mirren |
| Quarter Final | St. Johnstone | 1-2 | Brechin City |
12th August 2003
| 2nd Round | Brechin City | 3-1 | Stirling Albion |
| 2nd Round | Clyde | 0-1 | St. Johnstone |
| 2nd Round | Forfar Athletic | 4-2 | Albion Rovers |
| 2nd Round | Greenock Morton | 1-2 | Airdrie United |
| 2nd Round | Peterhead | 1-2 | Inverness Caledonian Thistle |
| 2nd Round | Raith Rovers | 2-0 | Stranraer |
| 2nd Round | Ross County | 5-0 | Dumbarton |
| 2nd Round | St. Mirren | 2-1 |
2nd August 2003
| 1st Round | Airdrie United | 2-0 | Montrose |
| 1st Round | Albion Rovers | 1-0 | East Fife |
| 1st Round | Alloa Athletic | 1-2 | Clyde |
| 1st Round | Ayr United | 1-2 | Stirling Albion |
| 1st Round | Brechin City | 1-0 | Falkirk |
| 1st Round | Cowdenbeath | 1-2 | Ross County |
| 1st Round | 2-5 | Raith Rovers |
| 1st Round | Forfar Athletic | 4-0 | Elgin City |
| 1st Round | 0-5 | Inverness Caledonian Thistle |
| 1st Round | 2-3 | St. Johnstone |
| 1st Round | Greenock Morton | 4-3 | Arbroath |
| 1st Round | St. Mirren | 3-2 | Queen's Park |
| 1st Round | Stenhousemuir | 0-3 | Peterhead |
| 1st Round | Stranraer | 2-1 | Queen of the South |