1988-89 Scottish Cup
| Final | ||||||
| Celtic | 1 | 0 | Rangers | Sat 20 May 1989 | Details | |
| Semi Final | ||||||
| Rangers | 0 | 0 | St Johnstone | Sat 15 Apr 1989 | Details | |
| Celtic | 3 | 1 | Hibernian | Sun 16 Apr 1989 | Details | |
| Rangers | 4 | 0 | St Johnstone | Tue 18 Apr 1989 | 1st Replay | Details |
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| 5th Round | ||||||
| Hibernian | 1 | 0 | Alloa Athletic | Mon 27 Feb 1989 | Details | |
| Celtic | 2 | 1 | Hearts | Sat 18 Mar 1989 | Details | |
| Rangers | 2 | 2 | Dundee United | Tue 21 Mar 1989 | Details | |
| Greenock Morton | 2 | 2 | St Johnstone | Wed 22 Mar 1989 | Details | |
| St Johnstone | 3 | 2 | Greenock Morton | Mon 27 Mar 1989 | 1st Replay | Details |
| Dundee United | 0 | 1 | Rangers | Mon 27 Mar 1989 | 1st Replay | Details |
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| 4th Round | ||||||
| Meadowbank Thistle | 0 | 1 | Greenock Morton | Sat 18 Feb 1989 | Details | |
| St Johnstone | 2 | 1 | Forfar Athletic | Sat 18 Feb 1989 | Details | |
| Aberdeen | 1 | 1 | Dundee United | Sat 18 Feb 1989 | Details | |
| Queen Of The South | 0 | 0 | Alloa Athletic | Sat 18 Feb 1989 | Details | |
| Celtic | 4 | 1 | Clydebank | Sat 18 Feb 1989 | Details | |
| Hibernian | 2 | 1 | Motherwell | Sat 18 Feb 1989 | Details | |
| Hearts | 2 | 0 | Partick Thistle | Sat 18 Feb 1989 | Details | |
| Rangers | 8 | 0 | Stranraer | Sat 18 Feb 1989 | Details | |
| Alloa Athletic | 4 | 2 | Queen Of The South | Wed 22 Feb 1989 | 1st Replay | Details |
| Dundee United | 1 | 1 | Aberdeen | Wed 22 Feb 1989 | 1st Replay | Details |
| Dundee United | 1 | 0 | Aberdeen | Mon 27 Feb 1989 | Details | |
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| 3rd Round | ||||||
| Hibernian | 1 | 0 | Brechin City | Sat 28 Jan 1989 | Details | |
| Falkirk | 1 | 1 | Motherwell | Sat 28 Jan 1989 | Details | |
| Dunfermline Athletic | 0 | 0 | Aberdeen | Sat 28 Jan 1989 | Details | |
| Greenock Morton | 0 | 0 | Airdrieonians | Sat 28 Jan 1989 | Details | |
| Raith Rovers | 1 | 1 | Rangers | Sat 28 Jan 1989 | Details | |
| Forfar Athletic | 1 | 1 | Clyde | Sat 28 Jan 1989 | Details | |
| Queen Of The South | 2 | 2 | Kilmarnock | Sat 28 Jan 1989 | Details | |
| Dundee | 1 | 2 | Dundee United | Sat 28 Jan 1989 | Details | |
| Partick Thistle | 0 | 0 | St Mirren | Sat 28 Jan 1989 | Details | |
| Queen's Park | 0 | 0 | Stranraer | Sat 28 Jan 1989 | Details | |
| St Johnstone | 2 | 0 | Stenhousemuir | Sat 28 Jan 1989 | Details | |
| Hearts | 4 | 1 | Ayr United | Sat 28 Jan 1989 | Details | |
| Celtic | 2 | 0 | Dumbarton | Sat 28 Jan 1989 | Details | |
| Alloa Athletic | 3 | 1 | Albion Rovers | Sat 28 Jan 1989 | Details | |
| Clydebank | 2 | 1 | Montrose | Sat 28 Jan 1989 | Details | |
| Meadowbank Thistle | 2 | 0 | Hamilton | Sun 29 Jan 1989 | Details | |
| St Mirren | 1 | 3 | Partick Thistle | Tue 31 Jan 1989 | 1st Replay | Details |
| Clyde | 0 | 1 | Forfar Athletic | Tue 31 Jan 1989 | 1st Replay | Details |
| Rangers | 3 | 0 | Raith Rovers | Tue 31 Jan 1989 | 1st Replay | Details |
| Stranraer | 1 | 0 | Queen's Park | Tue 31 Jan 1989 | 1st Replay | Details |
| Airdrieonians | 0 | 1 | Greenock Morton | Wed 01 Feb 1989 | 1st Replay | Details |
| Aberdeen | 3 | 1 | Dunfermline Athletic | Wed 01 Feb 1989 | 1st Replay | Details |
| Motherwell | 2 | 1 | Falkirk | Wed 01 Feb 1989 | 1st Replay | Details |
| Kilmarnock | 0 | 1 | Queen Of The South | Wed 01 Feb 1989 | 1st Replay | Details |
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| 2nd Round | ||||||
| Elgin City | 2 | 2 | Dumbarton | Sat 07 Jan 1989 | Details | |
| Annan Athletic | 1 | 5 | Queen's Park | Sat 07 Jan 1989 | Details | |
| Stranraer | 2 | 1 | East Fife | Sat 07 Jan 1989 | Details | |
| East Stirlingshire | 1 | 2 | Montrose | Sat 07 Jan 1989 | Details | |
| Forres Mechanics | 1 | 1 | Alloa Athletic | Sat 07 Jan 1989 | Details | |
| Caledonian | 1 | 1 | Brechin City | Sat 07 Jan 1989 | Details | |
| Cowdenbeath | 1 | 1 | Stenhousemuir | Sat 07 Jan 1989 | Details | |
| Coldstream | 1 | 1 | Albion Rovers | Sat 07 Jan 1989 | Details | |
| Brechin City | 2 | 1 | Caledonian | Sat 14 Jan 1989 | 1st Replay | Details |
| Stenhousemuir | 3 | 2 | Cowdenbeath | Sat 14 Jan 1989 | 1st Replay | Details |
| Alloa Athletic | 2 | 0 | Forres Mechanics | Sat 14 Jan 1989 | 1st Replay | Details |
| Albion Rovers | 1 | 0 | Coldstream | Sat 14 Jan 1989 | 1st Replay | Details |
| Dumbarton | 4 | 0 | Elgin City | Sat 14 Jan 1989 | 1st Replay | Details |
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| 1st Round | ||||||
| Stranraer | 2 | 2 | Stirling Albion | Sat 03 Dec 1988 | Details | |
| East Fife | 4 | 1 | Spartans | Sat 03 Dec 1988 | Details | |
| East Stirlingshire | 1 | 0 | Gala Fairydean | Sat 03 Dec 1988 | Details | |
| Inverness Thistle | 0 | 0 | Dumbarton | Sat 03 Dec 1988 | Details | |
| Berwick Rangers | 1 | 1 | Alloa Athletic | Sat 03 Dec 1988 | Details | |
| Montrose | 2 | 0 | Arbroath | Sat 03 Dec 1988 | Details | |
| Alloa Athletic | 2 | 1 | Berwick Rangers | Wed 07 Dec 1988 | 1st Replay | Details |
| Dumbarton | 2 | 1 | Inverness Thistle | Sat 10 Dec 1988 | 1st Replay | Details |
| Stirling Albion | 0 | 1 | Stranraer | Sat 10 Dec 1988 | 1st Replay | Details |
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