1965-66 Scottish Cup
| Final | ||||||
| Rangers | 0 | 0 | Celtic | Sat 23 Apr 1966 | Details | |
| Rangers | 1 | 0 | Celtic | Wed 27 Apr 1966 | 1st Replay | Details |
| Semi Final | ||||||
| Aberdeen | 0 | 0 | Rangers | Sat 26 Mar 1966 | Details | |
| Celtic | 2 | 0 | Dunfermline Athletic | Sat 26 Mar 1966 | Details | |
| Rangers | 2 | 1 | Aberdeen | Tue 29 Mar 1966 | 1st Replay | Details |
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| 3rd Round | ||||||
| Rangers | 1 | 0 | St Johnstone | Wed 23 Feb 1966 | Details | |
| Dumbarton | 0 | 3 | Aberdeen | Sat 05 Mar 1966 | Details | |
| Dunfermline Athletic | 2 | 1 | Kilmarnock | Sat 05 Mar 1966 | Details | |
| Hearts | 3 | 3 | Celtic | Sat 05 Mar 1966 | Details | |
| Celtic | 3 | 1 | Hearts | Wed 09 Mar 1966 | 1st Replay | Details |
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| 2nd Round | ||||||
| Kilmarnock | 5 | 0 | Motherwell | Mon 21 Feb 1966 | Details | |
| Hearts | 2 | 1 | Hibernian | Mon 21 Feb 1966 | Details | |
| Dumbarton | 1 | 0 | Queen Of The South | Wed 23 Feb 1966 | Details | |
| Aberdeen | 5 | 0 | Dundee United | Wed 23 Feb 1966 | Details | |
| Stirling Albion | 0 | 0 | Dunfermline Athletic | Wed 23 Feb 1966 | Details | |
| Dundee | 0 | 2 | Celtic | Wed 23 Feb 1966 | Details | |
| Ross County | 0 | 2 | Rangers | Mon 28 Feb 1966 | Details | |
| Dunfermline Athletic | 4 | 1 | Stirling Albion | Mon 28 Feb 1966 | 1st Replay | Details |
| Cowdenbeath | 3 | 3 | St Johnstone | Mon 28 Feb 1966 | Details | |
| St Johnstone | 3 | 0 | Cowdenbeath | Tue 01 Mar 1966 | 1st Replay | Details |
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| 1st Round | ||||||
| Hibernian | 4 | 3 | Third Lanark | Sat 05 Feb 1966 | Details | |
| Ayr United | 1 | 1 | St Johnstone | Sat 05 Feb 1966 | Details | |
| Hamilton | 1 | 3 | Aberdeen | Sat 05 Feb 1966 | Details | |
| Greenock Morton | 1 | 1 | Kilmarnock | Sat 05 Feb 1966 | Details | |
| Dunfermline Athletic | 3 | 1 | Partick Thistle | Sat 05 Feb 1966 | Details | |
| Celtic | 4 | 0 | Stranraer | Sat 05 Feb 1966 | Details | |
| Rangers | 5 | 1 | Airdrieonians | Sat 05 Feb 1966 | Details | |
| Queen Of The South | 3 | 0 | Albion Rovers | Sat 05 Feb 1966 | Details | |
| Stirling Albion | 3 | 1 | Queen's Park | Sat 05 Feb 1966 | Details | |
| Dundee United | 0 | 0 | Falkirk | Mon 07 Feb 1966 | Details | |
| Kilmarnock | 3 | 0 | Greenock Morton | Wed 09 Feb 1966 | 1st Replay | Details |
| Cowdenbeath | 1 | 0 | St Mirren | Wed 09 Feb 1966 | Details | |
| Dumbarton | 2 | 1 | Montrose | Wed 09 Feb 1966 | Details | |
| Hearts | 2 | 1 | Clyde | Wed 09 Feb 1966 | Details | |
| East Stirlingshire | 0 | 0 | Motherwell | Wed 09 Feb 1966 | Details | |
| Dundee | 9 | 1 | East Fife | Wed 09 Feb 1966 | Details | |
| Alloa Athletic | 3 | 5 | Ross County | Thu 10 Feb 1966 | Details | |
| Falkirk | 1 | 2 | Dundee United | Thu 10 Feb 1966 | 1st Replay | Details |
| Motherwell | 4 | 1 | East Stirlingshire | Mon 14 Feb 1966 | 1st Replay | Details |
| St Johnstone | 1 | 0 | Ayr United | Mon 14 Feb 1966 | 1st Replay | Details |
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| -1th Round | ||||||
| Berwick Rangers | 1 | 0 | Stenhousemuir | Sat 08 Jan 1966 | Details | |
| Forfar Athletic | 1 | 1 | Brechin City | Sat 08 Jan 1966 | Details | |
| Gala Fairydean | 6 | 1 | Selkirk | Sat 08 Jan 1966 | Details | |
| Dumbarton | 2 | 2 | Peebles Rovers | Sat 08 Jan 1966 | Details | |
| Raith Rovers | 1 | 0 | Caledonian | Sat 08 Jan 1966 | Details | |
| Brechin City | 1 | 3 | Forfar Athletic | Wed 12 Jan 1966 | 1st Replay | Details |
| Peebles Rovers | 2 | 3 | Dumbarton | Wed 12 Jan 1966 | 1st Replay | Details |
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| -2th Round | ||||||
| Berwick Rangers | 0 | 0 | Albion Rovers | Sat 22 Jan 1966 | Details | |
| East Fife | 1 | 0 | Elgin City | Sat 22 Jan 1966 | Details | |
| Glasgow University | 1 | 2 | Dumbarton | Sat 22 Jan 1966 | Details | |
| Gala Fairydean | 4 | 5 | Montrose | Sat 22 Jan 1966 | Details | |
| Ross County | 4 | 3 | Forfar Athletic | Sat 22 Jan 1966 | Details | |
| Arbroath | 2 | 2 | Cowdenbeath | Sat 22 Jan 1966 | Details | |
| Ayr United | 1 | 0 | Fraserburgh | Sat 22 Jan 1966 | Details | |
| Raith Rovers | 0 | 1 | Alloa Athletic | Sat 22 Jan 1966 | Details | |
| Cowdenbeath | 1 | 1 | Arbroath | Wed 26 Jan 1966 | 1st Replay | Details |
| Albion Rovers | 3 | 0 | Berwick Rangers | Wed 26 Jan 1966 | 1st Replay | Details |
| Arbroath | 2 | 3 | Cowdenbeath | Mon 31 Jan 1966 | 2nd Replay | Details |
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