Season 1988-89Celtic
 Qualifying Cup North First Round
Sep03  0-2  Peterhead v Buckie Thistle
Sep03  4-0  Forres Mechanics v Clachnacuddin
Sep03  0-2  Rothes v Elgin City
Sep03  8-0  Inverness Caledonian v Wick Academy
 Qualifying Cup North Second Round
Sep17  2-1  Cove Rangers v Brora Rangers
Sep17  1-1  Lossiemouth v Deveronvale
Sep24  2-1  Deveronvale v Lossiemouth
Sep17  2-1  Huntly v Buckie Thistle
Sep17  2-0  Fraserburgh v Ross County
Sep17  8-0  Elgin City v Golspie Sutherland
Sep17  0-6  Fort William v Inverness Thistle
Sep17  1-1  Forres Mechanics v Nairn County
Sep24  1-5  Nairn County v Forres Mechanics
Sep17  2-0  Inverness Caledonian v Keith
 Qualifying Cup North Third Round
Oct01  3-0  Inverness Thistle v Huntly
Oct01  4-1  Elgin City v Deveronvale
Oct01  1-1  Fraserburgh v Forres Mechanics
Oct08  3-0  Forres Mechanics v Fraserburgh
Oct01  3-0  Inverness Caledonian v Cove Rangers
 Qualifying Cup North Semi-finals – teams qualified for the cup proper
Oct15  1-1  Forres Mechanics v Inverness Caledonian
Oct22  5-0  Inverness Caledonian v Forres Mechanics
Oct15  6-2  Inverness Thistle v Elgin City
 Qualifying Cup North Final
Nov12  1-1  Inverness Caledonian v Inverness Thistle  at Kingsmills
Nov19  0-3  Inverness Caledonian v Inverness Thistle  at Telford Street
 First Round
Dec03  1-1  Berwick Rangers v Alloa Athletic
Dec07  2-1  Alloa Athletic v Berwick Rangers
Dec03  4-1  East Fife v Spartans
Dec03  1-0  East Stirlingshire v Gala Fairydean
Dec03  0-0  Inverness Thistle v Dumbarton
Dec10  2-1  Dumbarton v Inverness Thistle
Dec03  2-0  Montrose v Arbroath
Dec03  2-2  Stranraer v Stirling Albion
Dec10  0-1  Stirling Albion v Stranraer
 Second Round
Jan07  1-5  Annan Athletic v Queen’s Park
Jan07  1-1  Coldstream v Albion Rovers
Jan14  1-0  Albion Rovers v Coldstream
Jan07  1-1  Cowdenbeath v Stenhousemuir
Jan16  3-2  Stenhousemuir v Cowdenbeath
Jan07  1-2  East Stirlingshire v Montrose
Jan07  2-2  Elgin City v Dumbarton
Jan16  4-0  Dumbarton v Elgin City
Jan07  1-1  Forres Mechanics v Alloa Athletic
Jan14  2-0  Alloa Athletic v Forres Mechanics
Jan07  1-1  Inverness Caledonian v Brechin City
Jan14  2-1  Brechin City v Inverness Caledonian
Jan07  2-1  Stranraer v East Fife
 Third Round
Jan28  2-0  St Johnstone v Stenhousemuir
Jan28  0-0  Dunfermline Athletic v Aberdeen
Feb01  3-1  Aberdeen v Dunfermline Athletic
Jan28  2-0  Celtic v Dumbarton
Jan28  1-1  Falkirk v Motherwell
Feb01  2-1  Motherwell v Falkirk
Jan28  1-0  Hibernian v Brechin City
Jan28  2-2  Queen of the South v Kilmarnock
Feb01  0-1  Kilmarnock v Queen of the South
Jan28  3-1  Alloa Athletic v Albion Rovers
Jan29  2-0  Meadowbank Thistle v Hamilton Academical
Jan28  0-0  Queen’s Park v Stranraer
Feb01  1-0  Stranraer v Queen’s Park
Jan28  2-1  Clydebank v Montrose
Jan28  4-1  Heart of Midlothian v Ayr United
Jan28  1-1  Forfar Athletic v Clyde
Jan31  0-1  Clyde v Forfar Athletic
Jan28  1-1  Raith Rovers v Rangers
Feb01  3-0  Rangers v Raith Rovers
Jan28  0-0  Greenock Morton v Airdrieonians
Feb01  0-1  Airdrieonians v Greenock Morton
Jan28  0-0  Partick Thistle v St Mirren
Jan31  1-3  St Mirren v Partick Thistle
Jan28  1-2  Dundee v Dundee United
 Fourth Round
Feb18  4-1  Celtic v Clydebank
Feb18  0-0  Queen of the South v Alloa Athletic
Feb22  4-2  Alloa Athletic v Queen of the South
Feb18  2-0  Heart of Midlothian v Partick Thistle
Feb18  1-1  Aberdeen v Dundee United
Feb22  1-1  Dundee United v Aberdeen a.e.t. 0-0
Feb27  0-1  Aberdeen v Dundee United
Feb18  2-1  Hibernian v Motherwell
Feb18  8-0  Rangers v Stranraer
Feb18  2-1  St Johnstone v Forfar Athletic
Feb18  0-1  Meadowbank Thistle v Greenock Morton
 Fifth Round
Mar18  2-1  Celtic v Heart of Midlothian
Mar21  2-2  Rangers v Dundee United
Mar27  0-1  Dundee United v Rangers
Mar22  2-2  Greenock Morton v St Johnstone
Mar27  3-2  St Johnstone v Greenock Morton
Mar18  1-0  Hibernian v Alloa Athletic
 Semi-finals
Apr16  3-1  Celtic v Hibernian  at Hampden Park
Apr15  0-0  St Johnstone v Rangers  at Celtic Park
Apr18  0-4  St Johnstone v Rangers  at Celtic Park
 Final
May20  1-0  Celtic v Rangers  at Hampden Park