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1989-90 |

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Scottish Cup |
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Round One
- Berwick Rangers 1-1 Stenhousemuir
- Brechin City 3-1 Montrose
- Elgin City 2-1 Arbroath
- Queen's Park 1-2 Dumbarton
- Queen of the South 2-1 Cove Rangers
- Stirling Albion 4-0 Coldstream
Round One Replay
- Stenhousemuir 1-0 Berwick Rangers
Round Two
- Dumbarton 0-2 Cowdenbeath
- Elgin City 2-2 Brechin City
- Gala Fairydean 2-2 Inverness Caledonian
- Ross County 1-4 East Fife
- Stenhousemuir 0-1 Queen of the South
- Stirling Albion 3-0 Whitehill Welfare
- Stranraer 1-1 Kilmarnock
- Vale of Leithen 1-3 East Stirlingshire
Round Two Replays
- Brechin City 8-0 Elgin City
- Inverness Caledonian 4-1 Gala Fairydean
- Kilmarnock 0-0 Stranraer (Stranraer won 4-2 on penalties)
Round Three
- Airdrieonians 2-2 Inverness Caledonian
- Albion Rovers 0-2 Clydebank
- Ayr United 0-0 St Mirren
- Brechin City 0-2 Hibernian
- Cowdenbeath 3-1 Stranraer
- Dundee 0-0 Dundee United
- Dunfermline Athletic 0-0 Hamilton Academical
- East Fife 3-1 Meadowbank Thistle
- East Stirlingshire 0-1 Stirling Albion
- Forfar Athletic 1-2 Celtic
- Heart of Midlothian 2-0 Falkirk
- Morton 2-2 Raith Rovers
- Motherwell 7-0 Clyde
- Partick Thistle 2-6 Aberdeen
- Queen of the South 0-0 Alloa Athletic
- Rangers 3-0 St Johnstone
Round Three Replays
- Alloa Athletic 2-3 Queen of the South
- Dundee United 1-0 Dundee
- Hamilton Academical 0-1 Dunfermline Athletic
- Inverness Caledonian 1-1 Airdrieonians (Inverness Caledonian won 5-4 on penalties)
- Raith Rovers 1-3 Morton
- St Mirren 2-1 Ayr United
Round Four
- Aberdeen 2-1 Morton
- Celtic 1-0 Rangers
- Cowdenbeath 1-2 Dunfermline Athletic (@ Raith Rovers)
- Dundee United 2-1 Queen of the South
- Heart of Midlothian 4-0 Motherwell
- Hibernian 5-1 East Fife
- St Mirren 1-1 Clydebank
- Stirling Albion 6-2 Inverness Caledonian
Round Four Replay
Quarter Finals
- Aberdeen 4-1 Heart of Midlothian
- Clydebank 1-1 Stirling Albion
- Dundee United 1-0 Hibernian
- Dunfermline Athletic 0-0 Celtic
Quarter Final Replays
- Celtic 3-0 Dunfermline Athletic
- Stirling Albion 0-1 Clydebank (@ Falkirk)
Semi-finals
- Aberdeen 4-0 Dundee United (@ Heart of Midlothian)
- Celtic 2-0 Clydebank (@ Hampden Park)
Final (@ Hampden Park, 12/5/90)
- Aberdeen 0-0 Celtic (Aberdeen won 9-8 on penalties)
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