31st May 2003
| Final | Dundee | 0-1 | Rangers |
20th April 2003
| Semi Final | Inverness Caledonian Thistle | 0-1 | Dundee |
19th April 2003
| Semi Final | Rangers | 4-3 | Motherwell |
9th April 2003
| 5th Round Replay | Rangers | 3-0 | Dunfermline Athletic |
| 5th Round Replay | Dundee | 4-1 | Falkirk |
23rd March 2003
| 5th Round | Inverness Caledonian Thistle | 1-0 | Celtic |
| 5th Round | Dunfermline Athletic | 1-1 | Rangers |
22nd March 2003
| 5th Round | Stranraer | 0-4 | Motherwell |
| 5th Round | Falkirk | 1-1 | Dundee |
6th March 2003
| 4th Round Replay | Hibernian | 0-2 | Dunfermline Athletic |
23rd February 2003
| 4th Round | Celtic | 3-0 | St. Johnstone |
22nd February 2003
| 4th Round | Dundee | 2-0 | Aberdeen |
| 4th Round | Greenock Morton | 0-2 | Stranraer |
| 4th Round | Inverness Caledonian Thistle | 6-1 |
| 4th Round | Ayr United | 0-1 | Rangers |
| 4th Round | Clyde | 0-2 | Motherwell |
| 4th Round | Dunfermline Athletic | 1-1 | Hibernian |
| 4th Round | Alloa Athletic | 0-2 | Falkirk |
18th February 2003
| 3rd Round Replay | Aberdeen | 4-1 | Queen of the South |
17th February 2003
| 3rd Round Replay | Stranraer | 1-0 | Forfar Athletic |
10th February 2003
| 3rd Round Replay | 3-2 | Queen's Park |
4th February 2003
| 3rd Round Replay | St. Johnstone | 1-1 | Airdrie United |
| 3rd Round Replay | Dunfermline Athletic | 2-0 |
25th January 2003
| 3rd Round | Queen of the South | 0-0 | Aberdeen |
| 3rd Round | Cowdenbeath | 2-3 | Alloa Athletic |
| 3rd Round | 1-2 | Clyde |
| 3rd Round | Partick Thistle | 0-2 | Dundee |
| 3rd Round | 1-1 | Dunfermline Athletic |
| 3rd Round | Arbroath | 0-3 | Rangers |
| 3rd Round | Ross County | 1-2 | Greenock Morton |
| 3rd Round | Kilmarnock | 0-1 | Motherwell |
| 3rd Round | Falkirk | 4-0 | Heart of Midlothian |
| 3rd Round | Dundee United | 2-3 | Hibernian |
| 3rd Round | Ayr United | 2-0 | Peterhead |
| 3rd Round | Inverness Caledonian Thistle | 2-0 | Raith Rovers |
| 3rd Round | Airdrie United | 1-1 | St. Johnstone |
| 3rd Round | Celtic | 3-0 | St. Mirren |
| 3rd Round | Forfar Athletic | 2-2 | Stranraer |
20th January 2003
| 2nd Round Replay | East Fife | 2-2 |
15th January 2003
| 2nd Round | 1-1 | East Fife |
14th January 2003
| 2nd Round Replay | Albion Rovers | 0-2 | Queen's Park |
| 2nd Round | Airdrie United | 1-0 |
13th January 2003
| 2nd Round | Raith Rovers | 3-1 | Montrose |
| 2nd Round | Forfar Athletic | 3-1 | Stenhousemuir |
| 2nd Round | Stranraer | 4-1 | Stirling Albion |
| 2nd Round | Greenock Morton | 4-3 |
11th January 2003
| 2nd Round | Peterhead | 1-0 | Elgin City |
4th January 2003
| 2nd Round | 1-3 | Cowdenbeath |
| 2nd Round | Queen's Park | 1-1 | Albion Rovers |
| 2nd Round | 3-0 | Cove Rangers |
14th December 2002
| 1st Round Replay | 2-1 |
| 1st Round Replay | 2-3 | Stranraer |
7th December 2002
| 1st Round | Raith Rovers | 1-0 | Dumbarton |
| 1st Round | 0-1 |
| 1st Round | 1-4 | Cowdenbeath |
| 1st Round | Stenhousemuir | 4-1 | Brechin City |
| 1st Round | Montrose | 2-1 |
| 1st Round | Forfar Athletic | 3-1 |
| 1st Round | 1-1 |
| 1st Round | Stranraer | 1-1 |