Season 1989-90

First Round
Dec09 1-2 Queen's Park v Dumbarton
Dec09 1-1 Berwick Rangers v Stenhousemuir
Dec12 1-0 Stenhousemuir v Berwick Rangers
Dec09 3-1 Brechin City v Montrose
Dec09 2-1 Elgin City v Arbroath
Dec09 2-1 Queen of the South v Cove Rangers
Dec09 4-0 Stirling Albion v Coldstream
Second Round
Jan07 1-4 Ross County v East Fife
Dec30 3-0 Stirling Albion v Whitehill Welfare
Dec30 2-2 Elgin City v Brechin City
Jan06 8-0 Brechin City v Elgin City
Dec30 1-1 Stranraer v Kilmarnock
Jan06 0-0 Kilmarnock v Stranraer a.e.t. 0-0 pens 3-4
Dec30 1-3 Vale of Leithen v East Stirlingshire
Dec30 2-2 Gala Fairydean v Inverness Caledonian
Jan06 4-1 Inverness Caledonian v Gala Fairydean
Dec30 0-2 Dumbarton v Cowdenbeath
Dec30 0-1 Stenhousemuir v Queen of the South
Third Round
Jan20 2-0 Heart of Midlothian v Falkirk
Jan20 0-0 Ayr United v St Mirren
Jan24 2-1 St Mirren v Ayr United
Jan20 0-0 Queen of the South v Alloa Athletic
Jan29 2-3 Alloa Athletic v Queen of the South a.e.t. 2-2
Jan20 0-0 Dunfermline Athletic v Hamilton Academical
Jan31 0-1 Hamilton Academical v Dunfermline Athletic
Jan20 2-2 Greenock Morton v Raith Rovers
Jan29 1-3 Raith Rovers v Greenock Morton
Jan20 3-0 Rangers v St Johnstone
Jan20 2-6 Partick Thistle v Aberdeen
Jan20 3-1 Cowdenbeath v Stranraer
Jan20 2-2 Airdrieonians v Inverness Caledonian
Jan24 1-1 Inverness Caledonian v Airdrieonians a.e.t. 1-1 pens 5-4
Jan20 3-1 East Fife v Meadowbank Thistle
Jan20 7-0 Motherwell v Clyde
Jan20 0-0 Dundee v Dundee United
Jan23 1-0 Dundee United v Dundee
Jan20 0-2 Albion Rovers v Clydebank
Jan29 0-1 East Stirlingshire v Stirling Albion
Jan20 1-2 Forfar Athletic v Celtic
Jan20 0-2 Brechin City v Hibernian
Fourth Round
Feb28 1-1 St Mirren v Clydebank
Mar12 3-2 Clydebank v St Mirren
Feb27 1-2 Cowdenbeath v Dunfermline Athletic at Stark's Park
Feb26 2-1 Dundee United v Queen of the South
Feb24 2-1 Aberdeen v Greenock Morton
Feb25 1-0 Celtic v Rangers
Feb28 6-2 Stirling Albion v Inverness Caledonian
Feb24 4-0 Heart of Midlothian v Motherwell
Feb24 5-1 Hibernian v East Fife
Fifth Round
Mar17 1-0 Dundee United v Hibernian
Mar17 4-1 Aberdeen v Heart of Midlothian
Mar17 1-1 Clydebank v Stirling Albion
Mar21 0-1 Stirling Albion v Clydebank at Brockville Park
Mar17 0-0 Dunfermline Athletic v Celtic
Mar21 3-0 Celtic v Dunfermline Athletic
Semi-finals
Apr14 4-0 Aberdeen v Dundee United at Tynecastle Park
Apr14 2-0 Celtic v Clydebank at Hampden Park
Final
May12 0-0 Aberdeen v Celtic at Hampden Park a.e.t. 0-0 pens 9-8