22nd October 1989
| Final | Aberdeen | 2-1 | Rangers |
20th September 1989
| Semi Final | Aberdeen | 1-0 | Celtic |
19th September 1989
| Semi Final | Rangers | 5-0 | Dunfermline Athletic |
30th August 1989
| Quarter Final | Heart of Midlothian | 2-2 | Celtic |
| Quarter Final | 0-3 | Rangers |
| Quarter Final | Aberdeen | 3-1 | St. Mirren |
29th August 1989
| Quarter Final | Hibernian | 1-3 | Dunfermline Athletic |
23rd August 1989
| 3rd Round | St. Mirren | 1-0 | Motherwell |
| 3rd Round | Greenock Morton | 1-2 | Rangers |
| 3rd Round | 2-1 | Dundee United |
| 3rd Round | Falkirk | 1-4 | Heart of Midlothian |
| 3rd Round | Dunfermline Athletic | 1-0 | Dundee |
| 3rd Round | Aberdeen | 4-0 | Airdrie United |
22nd August 1989
| 3rd Round | Hibernian | 0-0 |
| 3rd Round | Celtic | 2-0 | Queen of the South |
16th August 1989
| 2nd Round | Queen of the South | 1-0 | St. Johnstone |
| 2nd Round | Heart of Midlothian | 3-0 | Montrose |
| 2nd Round | Dundee United | 1-0 | Partick Thistle |
| 2nd Round | 3-1 | Livingston |
| 2nd Round | Brechin City | 0-3 | Falkirk |
| 2nd Round | Albion Rovers | 0-2 | Aberdeen |
15th August 1989
| 2nd Round | Rangers | 4-0 | Arbroath |
| 2nd Round | Queen's Park | 0-1 | Greenock Morton |
| 2nd Round | Kilmarnock | 1-4 | Motherwell |
| 2nd Round | Hibernian | 2-0 | Alloa Athletic |
| 2nd Round | Dunfermline Athletic | 3-0 | Raith Rovers |
| 2nd Round | Dundee | 5-1 | Clyde |
| 2nd Round | Dumbarton | 0-3 | Celtic |
| 2nd Round | 0-2 | St. Mirren |
| 2nd Round | Ayr United | 0-1 |
| 2nd Round | Airdrie United | 4-0 | Forfar Athletic |
9th August 1989
| 1st Round | Stranraer | 3-4 | Brechin City |
| 1st Round | Stirling Albion | 0-3 |
| 1st Round | East Fife | 2-2 | Queen's Park |
| 1st Round | Cowdenbeath | 0-4 | Montrose |
| 1st Round | Arbroath | 1-0 |
8th August 1989
| 1st Round | Dumbarton | 3-0 | Stenhousemuir |