18th May 1991
| Final | Motherwell | 4-3 | Dundee United |
9th April 1991
| Semi Final Replay | Motherwell | 4-2 | Celtic |
6th April 1991
| Semi Final | Dundee United | 2-1 | St. Johnstone |
3rd April 1991
| Semi Final | Motherwell | 0-0 | Celtic |
19th March 1991
| 5th Round Replay | Greenock Morton | 1-1 | Motherwell |
17th March 1991
| 5th Round | Celtic | 2-0 | Rangers |
16th March 1991
| 5th Round | Motherwell | 0-0 | Greenock Morton |
| 5th Round | St. Johnstone | 5-2 | Ayr United |
13th March 1991
| 5th Round | Dundee United | 3-1 | Dundee |
2nd March 1991
| 4th Round | Greenock Morton | 3-0 | Livingston |
27th February 1991
| 4th Round Replay | 2-3 | Ayr United |
26th February 1991
| 4th Round | Celtic | 3-0 | St. Mirren |
23rd February 1991
| 4th Round | Ayr United | 0-0 |
| 4th Round | Dundee | 2-0 | Kilmarnock |
| 4th Round | Motherwell | 4-2 | Falkirk |
| 4th Round | Rangers | 5-0 | Cowdenbeath |
| 4th Round | St. Johnstone | 2-1 | Hibernian |
| 3rd Round | Ross County | 1-6 | Livingston |
| 4th Round | Dundee United | 2-0 | Airdrie United |
30th January 1991
| 3rd Round Replay | 3-4 | St. Johnstone |
| 3rd Round Replay | Falkirk | 4-3 | Partick Thistle |
29th January 1991
| 3rd Round | Rangers | 2-0 | Dunfermline Athletic |
| 3rd Round Replay | Dundee United | 2-1 | East Fife |
28th January 1991
| 3rd Round | Clyde | 0-2 | Hibernian |
| 2nd Round Replay | Queen of the South | 2-6 | Ross County |
26th January 1991
| 3rd Round | Forfar Athletic | 0-2 | Celtic |
| 3rd Round | East Fife | 1-1 | Dundee United |
| 3rd Round | Dundee | 1-0 | Brechin City |
| 3rd Round | St. Johnstone | 0-0 |
| 3rd Round | 0-1 | Ayr United |
| 3rd Round | Airdrie United | 2-1 | Heart of Midlothian |
| 3rd Round | Aberdeen | 0-1 | Motherwell |
| 3rd Round | Cove Rangers | 1-2 | Cowdenbeath |
| 3rd Round | Stranraer | 1-5 | St. Mirren |
| 3rd Round | Stirling Albion | 0-1 | Greenock Morton |
| 3rd Round | Raith Rovers | 0-1 |
| 3rd Round | Partick Thistle | 0-0 | Falkirk |
| 3rd Round | Kilmarnock | 3-2 | Arbroath |
23rd January 1991
| 2nd Round | Ross County | 2-2 | Queen of the South |
21st January 1991
| 2nd Round Replay | Cowdenbeath | 2-0 |
9th January 1991
| 2nd Round | 0-0 | Cowdenbeath |
7th January 1991
| 2nd Round Replay | East Fife | 1-0 |
5th January 1991
| 2nd Round | 1-1 | East Fife |
29th December 1990
| 2nd Round | 1-0 | Albion Rovers |
| 2nd Round | 1-4 | Cove Rangers |
| 2nd Round | Montrose | 0-2 | Arbroath |
| 2nd Round | Queen's Park | 1-2 | Stranraer |
| 2nd Round | Stirling Albion | 2-0 | Stenhousemuir |
17th December 1990
| 1st Round Replay | Dumbarton | 1-4 | Montrose |
15th December 1990
| 1st Round Replay | Alloa Athletic | 1-3 | Ross County |
| 1st Round | 1-2 |
| 1st Round | 0-4 | East Fife |
11th December 1990
| 1st Round | Montrose | 0-0 | Dumbarton |
8th December 1990
| 1st Round | 1-3 | Queen of the South |
| 1st Round | 3-1 |
| 1st Round | Ross County | 1-1 | Alloa Athletic |