26th October 1986
| Final | Rangers | 2-1 | Celtic |
24th September 1986
| Semi Final | Rangers | 2-1 | Dundee United |
23rd September 1986
| Semi Final | Motherwell | 2-2 | Celtic |
3rd September 1986
| Quarter Final | Rangers | 3-1 | Dundee |
| Quarter Final | Motherwell | 2-1 | Forfar Athletic |
| Quarter Final | Hibernian | 1-2 | Dundee United |
| Quarter Final | Aberdeen | 1-1 | Celtic |
27th August 1986
| 3rd Round | Dundee | 4-0 | Montrose |
| 3rd Round | East Fife | 0-0 | Rangers |
| 3rd Round | Forfar Athletic | 5-1 | St. Mirren |
| 3rd Round | 0-1 | Hibernian |
| 3rd Round | Motherwell | 2-0 |
| 3rd Round | Celtic | 3-0 | Dumbarton |
| 3rd Round | Ayr United | 0-3 | Dundee United |
| 3rd Round | Aberdeen | 3-1 | Clyde |
20th August 1986
| 2nd Round | 3-0 | St. Johnstone |
| 2nd Round | Celtic | 2-0 | Airdrie United |
| 2nd Round | Albion Rovers | 2-2 | Forfar Athletic |
| 2nd Round | Aberdeen | 4-0 | Alloa Athletic |
| 2nd Round | Stenhousemuir | 1-4 | Rangers |
| 2nd Round | Queen of the South | 0-1 | Dundee United |
| 2nd Round | Partick Thistle | 0-1 | East Fife |
| 2nd Round | Motherwell | 4-0 | Arbroath |
| 2nd Round | Greenock Morton | 2-5 | Dundee |
| 2nd Round | Kilmarnock | 1-2 | Ayr United |
| 2nd Round | Hibernian | 1-0 |
| 2nd Round | Dunfermline Athletic | 0-2 | St. Mirren |
| 2nd Round | Dumbarton | 1-0 | Stirling Albion |
19th August 1986
| 2nd Round | Clyde | 2-1 | Falkirk |
| 2nd Round | Brechin City | 0-1 |
| 2nd Round | Heart of Midlothian | 0-2 | Montrose |
13th August 1986
| 1st Round | Arbroath | 2-1 | Raith Rovers |
| 1st Round | Cowdenbeath | 0-1 | St. Johnstone |
| 1st Round | 1-4 | Stirling Albion |
| 1st Round | Stenhousemuir | 1-0 | Queen's Park |
| 1st Round | Stranraer | 0-2 |
12th August 1986
| 1st Round | Albion Rovers | 3-1 |