1968-69 Scottish Cup
| Final | ||||||
| Celtic | 4 | 0 | Rangers | Sat 26 Apr 1969 | Details | |
| Semi Final | ||||||
| Celtic | 4 | 1 | Greenock Morton | Sat 22 Mar 1969 | Details | |
| Rangers | 6 | 1 | Aberdeen | Sat 22 Mar 1969 | Details | |
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| 3rd Round | ||||||
| Rangers | 1 | 0 | Airdrieonians | Sat 01 Mar 1969 | Details | |
| Aberdeen | 0 | 0 | Kilmarnock | Sat 01 Mar 1969 | Details | |
| Dundee United | 2 | 3 | Greenock Morton | Sat 01 Mar 1969 | Details | |
| Celtic | 3 | 2 | St Johnstone | Sat 01 Mar 1969 | Details | |
| Kilmarnock | 0 | 3 | Aberdeen | Wed 05 Mar 1969 | 1st Replay | Details |
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| 2nd Round | ||||||
| Montrose | 1 | 1 | Kilmarnock | Sat 08 Feb 1969 | Details | |
| Stranraer | 1 | 3 | Greenock Morton | Sat 08 Feb 1969 | Details | |
| Dundee United | 6 | 2 | Ayr United | Sat 08 Feb 1969 | Details | |
| East Stirlingshire | 1 | 1 | St Johnstone | Sat 08 Feb 1969 | Details | |
| Kilmarnock | 4 | 1 | Greenock Morton | Wed 12 Feb 1969 | Details | |
| Clyde | 0 | 0 | Celtic | Wed 12 Feb 1969 | Details | |
| Airdrieonians | 1 | 1 | St Mirren | Wed 12 Feb 1969 | Details | |
| Celtic | 3 | 0 | Clyde | Mon 24 Feb 1969 | 1st Replay | Details |
| Rangers | 2 | 0 | Hearts | Mon 24 Feb 1969 | Details | |
| St Mirren | 1 | 3 | Airdrieonians | Mon 24 Feb 1969 | 1st Replay | Details |
| St Johnstone | 3 | 0 | East Stirlingshire | Mon 24 Feb 1969 | 1st Replay | Details |
| Aberdeen | 2 | 2 | Dunfermline Athletic | Tue 25 Feb 1969 | Details | |
| Dunfermline Athletic | 0 | 2 | Aberdeen | Wed 26 Feb 1969 | 1st Replay | Details |
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| 1st Round | ||||||
| Dundee United | 2 | 1 | Queen's Park | Sat 25 Jan 1969 | Details | |
| Stenhousemuir | 0 | 3 | Airdrieonians | Sat 25 Jan 1969 | Details | |
| Dumbarton | 0 | 1 | St Mirren | Sat 25 Jan 1969 | Details | |
| Stranraer | 3 | 1 | East Fife | Sat 25 Jan 1969 | Details | |
| East Stirlingshire | 2 | 0 | Stirling Albion | Sat 25 Jan 1969 | Details | |
| St Johnstone | 3 | 2 | Arbroath | Sat 25 Jan 1969 | Details | |
| Aberdeen | 3 | 0 | Berwick Rangers | Sat 25 Jan 1969 | Details | |
| Rangers | 1 | 0 | Hibernian | Sat 25 Jan 1969 | Details | |
| Motherwell | 1 | 1 | Clyde | Sat 25 Jan 1969 | Details | |
| Montrose | 1 | 0 | Cowdenbeath | Sat 25 Jan 1969 | Details | |
| Kilmarnock | 6 | 0 | Glasgow University | Sat 25 Jan 1969 | Details | |
| Dundee | 1 | 2 | Hearts | Sat 25 Jan 1969 | Details | |
| Partick Thistle | 3 | 3 | Celtic | Sat 25 Jan 1969 | Details | |
| Raith Rovers | 0 | 2 | Dunfermline Athletic | Sat 25 Jan 1969 | Details | |
| Ayr United | 1 | 0 | Queen Of The South | Sat 25 Jan 1969 | Details | |
| Falkirk | 1 | 2 | Greenock Morton | Sat 25 Jan 1969 | Details | |
| Clyde | 2 | 1 | Motherwell | Tue 28 Jan 1969 | 1st Replay | Details |
| Celtic | 8 | 1 | Partick Thistle | Wed 29 Jan 1969 | 1st Replay | Details |
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| -1th Round | ||||||
| Forfar Athletic | 1 | 2 | Nairn County | Sat 14 Dec 1968 | Details | |
| Alloa Athletic | 6 | 1 | Ross County | Sat 14 Dec 1968 | Details | |
| St Cuthberts Wanderers | 1 | 0 | Civil Service Strollers | Sat 14 Dec 1968 | Details | |
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| -2th Round | ||||||
| Stenhousemuir | 1 | 0 | Albion Rovers | Sat 04 Jan 1969 | Details | |
| Glasgow University | 5 | 2 | St Cuthberts Wanderers | Sat 04 Jan 1969 | Details | |
| Stranraer | 2 | 0 | Elgin City | Sat 04 Jan 1969 | Details | |
| Dumbarton | 3 | 2 | Vale Of Leithen | Sat 04 Jan 1969 | Details | |
| Alloa Athletic | 0 | 0 | East Stirlingshire | Sat 04 Jan 1969 | Details | |
| Montrose | 6 | 1 | Fraserburgh | Sat 04 Jan 1969 | Details | |
| Hamilton | 0 | 2 | Cowdenbeath | Sat 04 Jan 1969 | Details | |
| Nairn County | 0 | 2 | Berwick Rangers | Sat 04 Jan 1969 | Details | |
| East Stirlingshire | 2 | 1 | Alloa Athletic | Wed 08 Jan 1969 | 1st Replay | Details |
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