1985-86 Scottish Cup
| Final | ||||||
| Aberdeen | 3 | 0 | Hearts | Sat 10 May 1986 | Details | |
| Semi Final | ||||||
| Hearts | 1 | 0 | Dundee United | Sat 05 Apr 1986 | Details | |
| Aberdeen | 3 | 0 | Hibernian | Sat 05 Apr 1986 | Details | |
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| 5th Round | ||||||
| Dundee | 2 | 2 | Aberdeen | Sat 08 Mar 1986 | Details | |
| Motherwell | 0 | 1 | Dundee United | Sat 08 Mar 1986 | Details | |
| Hibernian | 4 | 3 | Celtic | Sat 08 Mar 1986 | Details | |
| Hearts | 4 | 1 | St Mirren | Sun 09 Mar 1986 | Details | |
| Aberdeen | 2 | 1 | Dundee | Wed 12 Mar 1986 | 1st Replay | Details |
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| 4th Round | ||||||
| Celtic | 2 | 1 | Queen's Park | Sat 15 Feb 1986 | Details | |
| Dundee United | 1 | 1 | Kilmarnock | Sat 15 Feb 1986 | Details | |
| Arbroath | 0 | 1 | Aberdeen | Sat 15 Feb 1986 | Details | |
| Hibernian | 1 | 0 | Ayr United | Sun 16 Feb 1986 | Details | |
| Kilmarnock | 0 | 1 | Dundee United | Wed 19 Feb 1986 | 1st Replay | Details |
| Dundee | 2 | 0 | Airdrieonians | Wed 19 Feb 1986 | Details | |
| Hamilton | 1 | 2 | Hearts | Mon 03 Mar 1986 | Details | |
| St Mirren | 1 | 1 | Falkirk | Tue 04 Mar 1986 | Details | |
| Alloa Athletic | 1 | 2 | Motherwell | Wed 05 Mar 1986 | Details | |
| Falkirk | 0 | 3 | St Mirren | Wed 05 Mar 1986 | 1st Replay | Details |
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| 3rd Round | ||||||
| Berwick Rangers | 2 | 3 | Alloa Athletic | Sat 25 Jan 1986 | Details | |
| Dundee United | 4 | 0 | Greenock Morton | Sat 25 Jan 1986 | Details | |
| Arbroath | 0 | 0 | Clyde | Sat 25 Jan 1986 | Details | |
| East Fife | 1 | 1 | St Mirren | Sat 25 Jan 1986 | Details | |
| Hearts | 3 | 2 | Rangers | Sat 25 Jan 1986 | Details | |
| Celtic | 2 | 0 | St Johnstone | Sat 25 Jan 1986 | Details | |
| Queen's Park | 1 | 0 | Dumbarton | Sat 25 Jan 1986 | Details | |
| Motherwell | 1 | 1 | Brechin City | Sat 25 Jan 1986 | Details | |
| Kilmarnock | 1 | 0 | Stirling Albion | Sat 25 Jan 1986 | Details | |
| Clydebank | 0 | 0 | Falkirk | Sat 25 Jan 1986 | Details | |
| Airdrieonians | 0 | 0 | Partick Thistle | Sat 25 Jan 1986 | Details | |
| Ayr United | 1 | 0 | Stenhousemuir | Sat 25 Jan 1986 | Details | |
| Nairn County | 0 | 7 | Dundee | Sat 25 Jan 1986 | Details | |
| Hibernian | 2 | 0 | Dunfermline Athletic | Sun 26 Jan 1986 | Details | |
| Falkirk | 1 | 0 | Clydebank | Mon 03 Feb 1986 | 1st Replay | Details |
| Hamilton | 2 | 1 | Forfar Athletic | Mon 03 Feb 1986 | Details | |
| Partick Thistle | 1 | 2 | Airdrieonians | Mon 03 Feb 1986 | 1st Replay | Details |
| Clyde | 1 | 2 | Arbroath | Mon 03 Feb 1986 | 1st Replay | Details |
| St Mirren | 3 | 1 | East Fife | Tue 04 Feb 1986 | 1st Replay | Details |
| Aberdeen | 4 | 1 | Montrose | Wed 05 Feb 1986 | Details | |
| Brechin City | 1 | 1 | Motherwell | Tue 11 Feb 1986 | 1st Replay | Details |
| Brechin City | 0 | 2 | Motherwell | Wed 12 Feb 1986 | 2nd Replay | Details |
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| 2nd Round | ||||||
| Stranraer | 1 | 2 | Berwick Rangers | Sat 04 Jan 1986 | Details | |
| Stenhousemuir | 0 | 0 | Whitehill | Sat 04 Jan 1986 | Details | |
| Fort William | 0 | 0 | Stirling Albion | Sat 04 Jan 1986 | Details | |
| Queen's Park | 2 | 1 | Albion Rovers | Sat 04 Jan 1986 | Details | |
| Threave Rovers | 0 | 5 | Dunfermline Athletic | Sat 04 Jan 1986 | Details | |
| Stirling Albion | 6 | 0 | Fort William | Sat 11 Jan 1986 | 1st Replay | Details |
| Nairn County | 1 | 1 | Meadowbank Thistle | Sat 11 Jan 1986 | Details | |
| Whitehill | 2 | 3 | Stenhousemuir | Sat 11 Jan 1986 | 1st Replay | Details |
| Hawick Royal Albert | 1 | 2 | St Johnstone | Sat 11 Jan 1986 | Details | |
| Peterhead | 1 | 2 | Arbroath | Sat 11 Jan 1986 | Details | |
| Meadowbank Thistle | 1 | 2 | Nairn County | Mon 13 Jan 1986 | 1st Replay | Details |
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| 1st Round | ||||||
| Berwick Rangers | 0 | 0 | Cowdenbeath | Sat 07 Dec 1985 | Details | |
| Dunfermline Athletic | 2 | 0 | Raith Rovers | Sat 07 Dec 1985 | Details | |
| Albion Rovers | 8 | 1 | Gala Fairydean | Sat 07 Dec 1985 | Details | |
| St Johnstone | 1 | 0 | Queen Of The South | Sat 07 Dec 1985 | Details | |
| Meadowbank Thistle | 3 | 2 | East Stirlingshire | Sat 07 Dec 1985 | Details | |
| Queen's Park | 3 | 0 | Buckie Thistle | Sat 07 Dec 1985 | Details | |
| Cowdenbeath | 0 | 2 | Berwick Rangers | Wed 11 Dec 1985 | 1st Replay | Details |
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