27th October 1991
| Final | Hibernian | 2-0 | Dunfermline Athletic |
25th September 1991
| Semi Final | Hibernian | 1-0 | Rangers |
24th September 1991
| Semi Final | Dunfermline Athletic | 1-1 | Airdrie United |
4th September 1991
| Quarter Final | Heart of Midlothian | 0-1 | Rangers |
3rd September 1991
| Quarter Final | Dunfermline Athletic | 3-1 | Dundee United |
| Quarter Final | Ayr United | 0-2 | Hibernian |
| Quarter Final | Airdrie United | 0-0 | Celtic |
28th August 1991
| 3rd Round | Partick Thistle | 0-2 | Rangers |
| 3rd Round | Kilmarnock | 2-3 | Hibernian |
| 3rd Round | 0-2 | Heart of Midlothian |
| 3rd Round | Dunfermline Athletic | 1-1 | St. Mirren |
| 3rd Round | Aberdeen | 0-1 | Airdrie United |
27th August 1991
| 3rd Round | Dundee United | 1-0 | Falkirk |
| 3rd Round | Celtic | 3-1 | Raith Rovers |
| 3rd Round | Ayr United | 2-0 | St. Johnstone |
26th August 1991
| 2nd Round | Cowdenbeath | 0-1 | Kilmarnock |
21st August 1991
| 2nd Round | Greenock Morton | 2-4 | Celtic |
| 2nd Round | 0-2 | St. Johnstone |
| 2nd Round | Dundee | 2-4 | Ayr United |
| 2nd Round | Clyde | 0-4 | Aberdeen |
| 1st Round Replay | Cowdenbeath | 1-0 | Arbroath |
20th August 1991
| 2nd Round | Stirling Albion | 0-3 | Hibernian |
| 2nd Round | Rangers | 6-0 | Queen's Park |
| 2nd Round | Raith Rovers | 4-1 | Motherwell |
| 2nd Round | Partick Thistle | 2-0 | Albion Rovers |
| 2nd Round | Heart of Midlothian | 3-0 |
| 2nd Round | 2-0 | Forfar Athletic |
| 2nd Round | Falkirk | 3-0 |
| 2nd Round | Dunfermline Athletic | 4-1 | Alloa Athletic |
| 2nd Round | Dundee United | 3-2 | Montrose |
| 2nd Round | Dumbarton | 1-2 | Airdrie United |
| 2nd Round | Brechin City | 3-3 | St. Mirren |
14th August 1991
| 1st Round | Cowdenbeath | 5-1 | Arbroath |
| 1st Round | 0-1 | Dumbarton |
13th August 1991
| 1st Round | Queen's Park | 4-2 | Stenhousemuir |
| 1st Round | Queen of the South | 0-4 | Albion Rovers |
| 1st Round | East Fife | 2-2 |
| 1st Round | Alloa Athletic | 0-0 | Stranraer |