16th May 1987
| Final | St. Mirren | 1-0 | Dundee United |
11th April 1987
| Semi Final | Heart of Midlothian | 1-2 | St. Mirren |
| Semi Final | Dundee | 2-3 | Dundee United |
24th March 1987
| 5th Round Replay | Forfar Athletic | 0-2 | Dundee United |
17th March 1987
| 5th Round Replay | Motherwell | 0-1 | Heart of Midlothian |
14th March 1987
| 5th Round | 0-4 | Dundee |
| 5th Round | Dundee United | 2-2 | Forfar Athletic |
| 5th Round | Raith Rovers | 0-2 | St. Mirren |
| 5th Round | Heart of Midlothian | 1-1 | Motherwell |
2nd March 1987
| 4th Round 2nd Replay | Dundee | 2-0 | Livingston |
| 4th Round 2nd Replay | Raith Rovers | 3-0 | Peterhead |
25th February 1987
| 4th Round Replay | Livingston | 1-1 | Dundee |
| 4th Round Replay | Peterhead | 3-3 | Raith Rovers |
21st February 1987
| 4th Round | Brechin City | 0-1 | Dundee United |
| 4th Round | Dundee | 1-1 | Livingston |
| 4th Round | 1-2 | Motherwell |
| 4th Round | Heart of Midlothian | 1-0 | Celtic |
| 4th Round | Greenock Morton | 2-3 | St. Mirren |
| 4th Round | Raith Rovers | 2-2 | Peterhead |
| 4th Round | St. Johnstone | 1-2 | Forfar Athletic |
| 4th Round | 1-0 | Hibernian |
9th February 1987
| 3rd Round 2nd Replay | Aberdeen | 0-1 | Celtic |
| 3rd Round 2nd Replay | Kilmarnock | 1-3 | Heart of Midlothian |
| 3rd Round Replay | 3-1 | Falkirk |
| 3rd Round Replay | East Fife | 1-4 | Dundee |
| 3rd Round Replay | Airdrie United | 1-2 | Dundee United |
7th February 1987
| 3rd Round | St. Johnstone | 4-0 |
4th February 1987
| 2nd Round | Albion Rovers | 1-2 |
| 3rd Round Replay | Celtic | 0-0 | Aberdeen |
| 3rd Round Replay | Dumbarton | 2-3 | Brechin City |
| 3rd Round Replay | Kilmarnock | 1-1 | Heart of Midlothian |
3rd February 1987
| 3rd Round | Dundee | 2-2 | East Fife |
| 3rd Round | Motherwell | 3-1 | Partick Thistle |
| 3rd Round | Livingston | 2-0 | Ayr United |
| 3rd Round | Falkirk | 0-0 |
1st February 1987
| 3rd Round | Aberdeen | 2-2 | Celtic |
31st January 1987
| 3rd Round | Heart of Midlothian | 0-0 | Kilmarnock |
| 3rd Round | Hibernian | 2-0 | Dunfermline Athletic |
| 3rd Round | Montrose | 1-2 | Forfar Athletic |
| 3rd Round | Dundee United | 1-1 | Airdrie United |
| 3rd Round | Peterhead | 2-0 | Clyde |
| 3rd Round | Queen of the South | 0-1 | Raith Rovers |
| 3rd Round | Rangers | 0-1 |
| 3rd Round | St. Mirren | 3-0 |
| 3rd Round | 0-2 | Greenock Morton |
| 3rd Round | Brechin City | 2-2 | Dumbarton |
28th January 1987
| 2nd Round Replay | 2-0 | Stenhousemuir |
26th January 1987
| 2nd Round | Raith Rovers | 4-0 |
| 2nd Round | St. Johnstone | 4-1 | Queen's Park |
| 2nd Round | Stenhousemuir | 0-0 |
21st January 1987
| 2nd Round Replay | Ayr United | 2-0 | Stranraer |
| 2nd Round | Stirling Albion | 0-1 | Livingston |
19th January 1987
| 2nd Round | 5-0 |
10th January 1987
| 2nd Round | 1-3 | Peterhead |
| 2nd Round | Stranraer | 1-1 | Ayr United |
13th December 1986
| 1st Round Replay | Alloa Athletic | 0-1 |
| 1st Round | 0-1 |
6th December 1986
| 1st Round | Stirling Albion | 3-0 | Cowdenbeath |
| 1st Round | Albion Rovers | 2-1 | Arbroath |
| 1st Round | Ayr United | 3-1 | Annan Athletic |
| 1st Round | 2-2 | Alloa Athletic |
| 1st Round | Peterhead | 1-0 |