12th May 1990
| Final | Aberdeen | 0-0 | Celtic |
14th April 1990
| Semi Final | Celtic | 2-0 |
| Semi Final | Aberdeen | 4-0 | Dundee United |
21st March 1990
| 5th Round Replay | Stirling Albion | 0-1 |
| 5th Round Replay | Celtic | 3-0 | Dunfermline Athletic |
17th March 1990
| 5th Round | 1-1 | Stirling Albion |
| 5th Round | Dunfermline Athletic | 0-0 | Celtic |
| 5th Round | Dundee United | 1-0 | Hibernian |
| 5th Round | Aberdeen | 4-1 | Heart of Midlothian |
12th March 1990
| 4th Round Replay | 3-2 | St. Mirren |
28th February 1990
| 4th Round | St. Mirren | 1-1 |
| 4th Round | Stirling Albion | 6-2 |
27th February 1990
| 4th Round | Cowdenbeath | 1-2 | Dunfermline Athletic |
26th February 1990
| 4th Round | Dundee United | 2-1 | Queen of the South |
25th February 1990
| 4th Round | Celtic | 1-0 | Rangers |
24th February 1990
| 4th Round | Aberdeen | 2-1 | Greenock Morton |
| 4th Round | Heart of Midlothian | 4-0 | Motherwell |
| 4th Round | Hibernian | 5-1 | East Fife |
31st January 1990
| 3rd Round Replay | 0-1 | Dunfermline Athletic |
29th January 1990
| 3rd Round Replay | Alloa Athletic | 2-3 | Queen of the South |
| 3rd Round Replay | Raith Rovers | 1-3 | Greenock Morton |
| 3rd Round | 0-1 | Stirling Albion |
24th January 1990
| 3rd Round Replay | St. Mirren | 2-1 | Ayr United |
| 3rd Round Replay | 1-1 | Airdrie United |
23rd January 1990
| 3rd Round Replay | Dundee United | 1-0 | Dundee |
20th January 1990
| 3rd Round | East Fife | 3-1 | Livingston |
| 3rd Round | Dunfermline Athletic | 0-0 |
| 3rd Round | Dundee | 0-0 | Dundee United |
| 3rd Round | Cowdenbeath | 3-1 | Stranraer |
| 3rd Round | Greenock Morton | 2-2 | Raith Rovers |
| 3rd Round | Ayr United | 0-0 | St. Mirren |
| 3rd Round | Albion Rovers | 0-2 |
| 3rd Round | Airdrie United | 2-2 |
| 3rd Round | Brechin City | 0-2 | Hibernian |
| 3rd Round | Rangers | 3-0 | St. Johnstone |
| 3rd Round | Queen of the South | 0-0 | Alloa Athletic |
| 3rd Round | Partick Thistle | 2-6 | Aberdeen |
| 3rd Round | Motherwell | 7-0 | Clyde |
| 3rd Round | Heart of Midlothian | 2-0 | Falkirk |
| 3rd Round | Forfar Athletic | 1-2 | Celtic |
7th January 1990
| 2nd Round | Ross County | 1-4 | East Fife |
6th January 1990
| 2nd Round Replay | 4-1 |
| 2nd Round Replay | Kilmarnock | 0-0 | Stranraer |
| 2nd Round Replay | Brechin City | 8-0 | Elgin City |
30th December 1989
| 2nd Round | 2-2 |
| 2nd Round | Stenhousemuir | 0-1 | Queen of the South |
| 2nd Round | Stirling Albion | 3-0 |
| 2nd Round | Stranraer | 1-1 | Kilmarnock |
| 2nd Round | 1-3 |
| 2nd Round | Dumbarton | 0-2 | Cowdenbeath |
| 2nd Round | Elgin City | 2-2 | Brechin City |
12th December 1989
| 1st Round Replay | Stenhousemuir | 1-0 |
9th December 1989
| 1st Round | 1-1 | Stenhousemuir |
| 1st Round | Brechin City | 3-1 | Montrose |
| 1st Round | Elgin City | 2-1 | Arbroath |
| 1st Round | Queen of the South | 2-1 | Cove Rangers |
| 1st Round | Queen's Park | 1-2 | Dumbarton |
| 1st Round | Stirling Albion | 4-0 |