23rd October 1988
| Final | Rangers | 3-2 | Aberdeen |
21st September 1988
| Semi Final | Rangers | 3-0 | Heart of Midlothian |
20th September 1988
| Semi Final | Aberdeen | 2-0 | Dundee United |
31st August 1988
| Quarter Final | Dundee United | 2-0 | Celtic |
| Quarter Final | Rangers | 4-1 | Dundee |
| Quarter Final | Dunfermline Athletic | 1-4 | Heart of Midlothian |
| Quarter Final | Hibernian | 1-2 | Aberdeen |
24th August 1988
| 3rd Round | Dundee | 2-1 | Falkirk |
| 3rd Round | Celtic | 7-2 |
| 3rd Round | Rangers | 6-0 |
| 3rd Round | Dunfermline Athletic | 2-1 | Motherwell |
| 3rd Round | St. Mirren | 1-3 | Dundee United |
23rd August 1988
| 3rd Round | Greenock Morton | 1-2 | Aberdeen |
| 3rd Round | Hibernian | 1-0 | Kilmarnock |
| 3rd Round | 0-2 | Heart of Midlothian |
17th August 1988
| 2nd Round | 2-0 | Stenhousemuir |
| 2nd Round | Dundee | 5-1 | Queen of the South |
| 2nd Round | East Fife | 1-1 | Dunfermline Athletic |
| 2nd Round | Falkirk | 1-1 | Raith Rovers |
| 2nd Round | Celtic | 4-1 | Ayr United |
| 2nd Round | Heart of Midlothian | 5-0 | St. Johnstone |
| 2nd Round | Aberdeen | 4-0 | Arbroath |
| 2nd Round | Airdrie United | 0-1 | Motherwell |
| 2nd Round | Hibernian | 4-0 | Stranraer |
| 2nd Round | Kilmarnock | 1-0 | Forfar Athletic |
| 2nd Round | Brechin City | 0-2 | Greenock Morton |
| 2nd Round | Clyde | 0-3 | Rangers |
16th August 1988
| 2nd Round | Dumbarton | 1-3 | St. Mirren |
| 2nd Round | Albion Rovers | 2-4 |
| 2nd Round | 2-1 | Stirling Albion |
| 2nd Round | Partick Thistle | 0-2 | Dundee United |
11th August 1988
| 1st Round | 0-1 | Arbroath |
10th August 1988
| 1st Round | Cowdenbeath | 0-0 | Albion Rovers |
| 1st Round | Brechin City | 3-1 | Montrose |
| 1st Round | Alloa Athletic | 2-4 | Stirling Albion |
| 1st Round | Queen's Park | 1-2 | Stranraer |
| 1st Round | Stenhousemuir | 3-0 |