28th October 1990
| Final | Rangers | 2-1 | Celtic |
26th September 1990
| Semi Final | Rangers | 1-0 | Aberdeen |
25th September 1990
| Semi Final | Celtic | 2-0 | Dundee United |
5th September 1990
| Quarter Final | Celtic | 2-1 | Queen of the South |
| Quarter Final | Aberdeen | 3-0 | Heart of Midlothian |
4th September 1990
| Quarter Final | Rangers | 6-2 | Raith Rovers |
| Quarter Final | Dundee United | 2-0 | Motherwell |
29th August 1990
| 3rd Round | St. Mirren | 0-1 | Heart of Midlothian |
| 3rd Round | Raith Rovers | 1-0 | Hibernian |
| 3rd Round | 0-1 | Celtic |
| 3rd Round | Aberdeen | 4-0 | Stranraer |
28th August 1990
| 3rd Round | Rangers | 1-0 | Kilmarnock |
| 3rd Round | Partick Thistle | 1-3 | Dundee United |
| 3rd Round | Motherwell | 2-0 | Clyde |
| 3rd Round | Dunfermline Athletic | 1-2 | Queen of the South |
22nd August 1990
| 2nd Round | St. Mirren | 1-0 | Arbroath |
| 2nd Round | Livingston | 0-1 | Hibernian |
| 2nd Round | Falkirk | 1-1 | Partick Thistle |
| 2nd Round | Cowdenbeath | 0-2 | Heart of Midlothian |
| 2nd Round | Celtic | 4-0 | Ayr United |
21st August 1990
| 2nd Round | St. Johnstone | 0-2 | Clyde |
| 2nd Round | Rangers | 5-0 |
| 2nd Round | Queen's Park | 1-2 | Aberdeen |
| 2nd Round | Queen of the South | 2-2 | Dundee |
| 2nd Round | Motherwell | 4-3 | Greenock Morton |
| 2nd Round | Kilmarnock | 3-2 |
| 2nd Round | Forfar Athletic | 1-2 | Raith Rovers |
| 2nd Round | Dunfermline Athletic | 4-0 | Albion Rovers |
| 2nd Round | Brechin City | 0-2 |
| 2nd Round | Alloa Athletic | 0-3 | Dundee United |
| 2nd Round | Airdrie United | 1-2 | Stranraer |
15th August 1990
| 1st Round | Stranraer | 4-3 |
| 1st Round | Stirling Albion | 1-2 | Arbroath |
| 1st Round | Montrose | 1-2 | Queen of the South |
14th August 1990
| 1st Round | Stenhousemuir | 0-2 | Cowdenbeath |
| 1st Round | Queen's Park | 3-3 | East Fife |
| 1st Round | 2-2 | Dumbarton |