Season 1989-90Aberdeen
 Qualifying Cup North First Round
Sep02  3-2  Buckie Thistle v Forres Mechanics
Sep02  3-2  Huntly v Wick Academy
Sep02  5-0  Inverness Caledonian v Rothes
Sep02  1-2  Inverness Thistle v Lossiemouth
 Qualifying Cup North Second Round
Sep16  1-1  Brora Rangers v Cove Rangers
Sep23  3-1  Cove Rangers v Brora Rangers
Sep16  1-5  Clachnacuddin v Keith
Sep16  2-0  Elgin City v Huntly
Sep16  4-1  Fort William v Golspie Sutherland
Sep16  2-3  Fraserburgh v Inverness Caledonian
Sep16  4-1  Lossiemouth v Peterhead
Sep16  3-3  Nairn County v Deveronvale
Sep23  3-2  Deveronvale v Nairn County a.e.t. 2-2
Sep16  3-0  Ross County v Buckie Thistle
 Qualifying Cup North Third Round
Sep30  2-1  Cove Rangers v Lossiemouth
Sep30  4-1  Elgin City v Deveronvale
Sep30  1-1  Fort William v Inverness Caledonian
Oct07  4-0  Inverness Caledonian v Fort William
Sep30  4-3  Ross County v Keith
 Qualifying Cup North Semi-finals – teams qualified for the cup proper
Oct14  3-2  Cove Rangers v Inverness Caledonian
Oct14  1-3  Ross County v Elgin City
 Qualifying Cup North Final
Nov04  0-1  Cove Rangers v Elgin City  at Kynoch Park
 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
Apr14  4-0  Aberdeen v Dundee United  at Tynecastle Park
Apr14  2-0  Celtic v Clydebank  at Hampden Park
May12  0-0  Aberdeen v Celtic  at Hampden Park a.e.t. 0-0 pens 9-8