1989-90 Scottish Cup
| Final | ||||||
| Aberdeen | 0 | 0 | Celtic | Sat 12 May 1990 | Details | |
| Semi Final | ||||||
| Celtic | 2 | 0 | Clydebank | Sat 14 Apr 1990 | Details | |
| Aberdeen | 4 | 0 | Dundee United | Sat 14 Apr 1990 | Details | |
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| 5th Round | ||||||
| Aberdeen | 4 | 1 | Hearts | Sat 17 Mar 1990 | Details | |
| Clydebank | 1 | 1 | Stirling Albion | Sat 17 Mar 1990 | Details | |
| Dundee United | 1 | 0 | Hibernian | Sat 17 Mar 1990 | Details | |
| Dunfermline Athletic | 0 | 0 | Celtic | Sat 17 Mar 1990 | Details | |
| Celtic | 3 | 0 | Dunfermline Athletic | Wed 21 Mar 1990 | 1st Replay | Details |
| Stirling Albion | 0 | 1 | Clydebank | Wed 21 Mar 1990 | 1st Replay | Details |
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| 4th Round | ||||||
| Hearts | 4 | 0 | Motherwell | Sat 24 Feb 1990 | Details | |
| Aberdeen | 2 | 1 | Greenock Morton | Sat 24 Feb 1990 | Details | |
| Hibernian | 5 | 1 | East Fife | Sat 24 Feb 1990 | Details | |
| Celtic | 1 | 0 | Rangers | Sun 25 Feb 1990 | Details | |
| Dundee United | 2 | 1 | Queen Of The South | Mon 26 Feb 1990 | Details | |
| Cowdenbeath | 1 | 2 | Dunfermline Athletic | Tue 27 Feb 1990 | Details | |
| St Mirren | 1 | 1 | Clydebank | Wed 28 Feb 1990 | Details | |
| Stirling Albion | 6 | 2 | Caledonian | Wed 28 Feb 1990 | Details | |
| Clydebank | 3 | 2 | St Mirren | Mon 12 Mar 1990 | 1st Replay | Details |
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| 3rd Round | ||||||
| Hearts | 2 | 0 | Falkirk | Sat 20 Jan 1990 | Details | |
| Rangers | 3 | 0 | St Johnstone | Sat 20 Jan 1990 | Details | |
| Ayr United | 0 | 0 | St Mirren | Sat 20 Jan 1990 | Details | |
| Airdrieonians | 2 | 2 | Caledonian | Sat 20 Jan 1990 | Details | |
| Dundee | 0 | 0 | Dundee United | Sat 20 Jan 1990 | Details | |
| Motherwell | 7 | 0 | Clyde | Sat 20 Jan 1990 | Details | |
| Cowdenbeath | 3 | 1 | Stranraer | Sat 20 Jan 1990 | Details | |
| East Fife | 3 | 1 | Meadowbank Thistle | Sat 20 Jan 1990 | Details | |
| Greenock Morton | 2 | 2 | Raith Rovers | Sat 20 Jan 1990 | Details | |
| Queen Of The South | 0 | 0 | Alloa Athletic | Sat 20 Jan 1990 | Details | |
| Forfar Athletic | 1 | 2 | Celtic | Sat 20 Jan 1990 | Details | |
| Dunfermline Athletic | 0 | 0 | Hamilton | Sat 20 Jan 1990 | Details | |
| Brechin City | 0 | 2 | Hibernian | Sat 20 Jan 1990 | Details | |
| Albion Rovers | 0 | 2 | Clydebank | Sat 20 Jan 1990 | Details | |
| Partick Thistle | 2 | 6 | Aberdeen | Sat 20 Jan 1990 | Details | |
| Dundee United | 1 | 0 | Dundee | Tue 23 Jan 1990 | 1st Replay | Details |
| St Mirren | 2 | 1 | Ayr United | Wed 24 Jan 1990 | 1st Replay | Details |
| Caledonian | 1 | 1 | Airdrieonians | Wed 24 Jan 1990 | 1st Replay | Details |
| East Stirlingshire | 0 | 1 | Stirling Albion | Mon 29 Jan 1990 | Details | |
| Alloa Athletic | 2 | 3 | Queen Of The South | Mon 29 Jan 1990 | 1st Replay | Details |
| Raith Rovers | 1 | 3 | Greenock Morton | Mon 29 Jan 1990 | 1st Replay | Details |
| Hamilton | 0 | 1 | Dunfermline Athletic | Wed 31 Jan 1990 | 1st Replay | Details |
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| 2nd Round | ||||||
| Gala Fairydean | 2 | 2 | Caledonian | Sat 30 Dec 1989 | Details | |
| Stirling Albion | 3 | 0 | Whitehill | Sat 30 Dec 1989 | Details | |
| Stranraer | 1 | 1 | Kilmarnock | Sat 30 Dec 1989 | Details | |
| Dumbarton | 0 | 2 | Cowdenbeath | Sat 30 Dec 1989 | Details | |
| Elgin City | 2 | 2 | Brechin City | Sat 30 Dec 1989 | Details | |
| Stenhousemuir | 0 | 1 | Queen Of The South | Sat 30 Dec 1989 | Details | |
| Vale Of Leithen | 1 | 3 | East Stirlingshire | Sat 30 Dec 1989 | Details | |
| Brechin City | 8 | 0 | Elgin City | Sat 06 Jan 1990 | 1st Replay | Details |
| Caledonian | 4 | 1 | Gala Fairydean | Sat 06 Jan 1990 | 1st Replay | Details |
| Kilmarnock | 0 | 0 | Stranraer | Sat 06 Jan 1990 | 1st Replay | Details |
| Ross County | 1 | 4 | East Fife | Sun 07 Jan 1990 | Details | |
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| 1st Round | ||||||
| Elgin City | 2 | 1 | Arbroath | Sat 09 Dec 1989 | Details | |
| Queen's Park | 1 | 2 | Dumbarton | Sat 09 Dec 1989 | Details | |
| Stirling Albion | 4 | 0 | Coldstream | Sat 09 Dec 1989 | Details | |
| Brechin City | 3 | 1 | Montrose | Sat 09 Dec 1989 | Details | |
| Berwick Rangers | 1 | 1 | Stenhousemuir | Sat 09 Dec 1989 | Details | |
| Queen Of The South | 2 | 1 | Cove Rangers | Sat 09 Dec 1989 | Details | |
| Stenhousemuir | 1 | 0 | Berwick Rangers | Tue 12 Dec 1989 | 1st Replay | Details |
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