20th May 1989
| Final | Celtic | 1-0 | Rangers |
18th April 1989
| Semi Final Replay | Rangers | 4-0 | St. Johnstone |
16th April 1989
| Semi Final | Celtic | 3-1 | Hibernian |
15th April 1989
| Semi Final | Rangers | 0-0 | St. Johnstone |
27th March 1989
| 5th Round Replay | St. Johnstone | 3-2 | Greenock Morton |
| 5th Round Replay | Dundee United | 0-1 | Rangers |
22nd March 1989
| 5th Round | Greenock Morton | 2-2 | St. Johnstone |
21st March 1989
| 5th Round | Rangers | 2-2 | Dundee United |
18th March 1989
| 5th Round | Hibernian | 1-0 | Alloa Athletic |
| 5th Round | Celtic | 2-1 | Heart of Midlothian |
27th February 1989
| 4th Round 2nd Replay | Dundee United | 1-0 | Aberdeen |
22nd February 1989
| 4th Round Replay | Dundee United | 1-1 | Aberdeen |
| 4th Round Replay | Alloa Athletic | 4-2 | Queen of the South |
18th February 1989
| 4th Round | St. Johnstone | 2-1 | Forfar Athletic |
| 4th Round | Rangers | 8-0 | Stranraer |
| 4th Round | Queen of the South | 0-0 | Alloa Athletic |
| 4th Round | Livingston | 0-1 | Greenock Morton |
| 4th Round | Hibernian | 2-1 | Motherwell |
| 4th Round | Heart of Midlothian | 2-0 | Partick Thistle |
| 4th Round | Celtic | 4-1 |
| 4th Round | Aberdeen | 1-1 | Dundee United |
1st February 1989
| 3rd Round Replay | Stranraer | 1-0 | Queen's Park |
| 3rd Round Replay | Rangers | 3-0 | Raith Rovers |
| 3rd Round Replay | Motherwell | 2-1 | Falkirk |
| 3rd Round Replay | Kilmarnock | 0-1 | Queen of the South |
| 3rd Round Replay | Airdrie United | 0-1 | Greenock Morton |
| 3rd Round Replay | Aberdeen | 3-1 | Dunfermline Athletic |
31st January 1989
| 3rd Round Replay | St. Mirren | 1-3 | Partick Thistle |
| 3rd Round Replay | Clyde | 0-1 | Forfar Athletic |
29th January 1989
| 3rd Round | Livingston | 2-0 |
28th January 1989
| 3rd Round | St. Johnstone | 2-0 | Stenhousemuir |
| 3rd Round | Raith Rovers | 1-1 | Rangers |
| 3rd Round | Queen's Park | 0-0 | Stranraer |
| 3rd Round | Queen of the South | 2-2 | Kilmarnock |
| 3rd Round | Partick Thistle | 0-0 | St. Mirren |
| 3rd Round | Greenock Morton | 0-0 | Airdrie United |
| 3rd Round | Hibernian | 1-0 | Brechin City |
| 3rd Round | Heart of Midlothian | 4-1 | Ayr United |
| 3rd Round | Forfar Athletic | 1-1 | Clyde |
| 3rd Round | Falkirk | 1-1 | Motherwell |
| 3rd Round | Dunfermline Athletic | 0-0 | Aberdeen |
| 3rd Round | Dundee | 1-2 | Dundee United |
| 3rd Round | 2-1 | Montrose |
| 3rd Round | Celtic | 2-0 | Dumbarton |
| 3rd Round | Alloa Athletic | 3-1 | Albion Rovers |
14th January 1989
| 2nd Round Replay | Stenhousemuir | 3-2 | Cowdenbeath |
| 2nd Round Replay | Dumbarton | 4-0 | Elgin City |
| 2nd Round Replay | Brechin City | 2-1 |
| 2nd Round Replay | Alloa Athletic | 2-0 |
| 2nd Round Replay | Albion Rovers | 1-0 |
7th January 1989
| 2nd Round | Stranraer | 2-1 | East Fife |
| 2nd Round | 1-1 | Brechin City |
| 2nd Round | 1-1 | Alloa Athletic |
| 2nd Round | Elgin City | 2-2 | Dumbarton |
| 2nd Round | 1-2 | Montrose |
| 2nd Round | Cowdenbeath | 1-1 | Stenhousemuir |
| 2nd Round | 1-1 | Albion Rovers |
| 2nd Round | Annan Athletic | 1-5 | Queen's Park |
10th December 1988
| 1st Round Replay | Stirling Albion | 0-1 | Stranraer |
| 1st Round Replay | Dumbarton | 2-1 |
7th December 1988
| 1st Round Replay | Alloa Athletic | 2-1 |
3rd December 1988
| 1st Round | Stranraer | 2-2 | Stirling Albion |
| 1st Round | Montrose | 2-0 | Arbroath |
| 1st Round | 0-0 | Dumbarton |
| 1st Round | 1-0 |
| 1st Round | East Fife | 4-1 |
| 1st Round | 1-1 | Alloa Athletic |