Season 1968-69Celtic
 First Preliminary Round
Dec14  1-1  Brechin City v Montrose
Dec18  3-2  Montrose v Brechin City
Dec14  1-0  Cowdenbeath v Clydebank
Dec14  6-1  Alloa Athletic v Ross County
Dec14  1-0  St Cuthbert Wanderers v Civil Service Strollers
Dec14  1-2  Forfar Athletic v Nairn County
 Second Preliminary Round
Jan04  1-0  Stenhousemuir v Albion Rovers
Jan04  0-2  Hamilton Academical v Cowdenbeath
Jan04  3-2  Dumbarton v Vale of Leithen
Jan04  0-2  Nairn County v Berwick Rangers
Jan04  0-0  Alloa Athletic v East Stirlingshire
Jan08  2-1  East Stirlingshire v Alloa Athletic
Jan04  6-1  Montrose v Fraserburgh
Jan04  2-0  Stranraer v Elgin City
Jan04  5-2  Glasgow University v St Cuthbert Wanderers
 First Round
Jan25  0-1  Dumbarton v St Mirren
Jan25  2-0  East Stirlingshire v Stirling Albion
Jan25  3-1  Stranraer v East Fife
Jan25  1-0  Ayr United v Queen of the South
Jan25  1-1  Motherwell v Clyde
Jan28  2-1  Clyde v Motherwell
Jan25  6-0  Kilmarnock v Glasgow University
Jan25  1-0  Rangers v Hibernian
Jan25  1-2  Falkirk v Greenock Morton
Jan25  1-2  Dundee v Heart of Midlothian
Jan25  2-1  Dundee United v Queen’s Park
Jan25  3-3  Partick Thistle v Celtic
Jan29  8-1  Celtic v Partick Thistle
Jan25  0-2  Raith Rovers v Dunfermline Athletic
Jan25  1-0  Montrose v Cowdenbeath
Jan25  0-3  Stenhousemuir v Airdrieonians
Jan25  3-2  St Johnstone v Arbroath
Jan25  3-0  Aberdeen v Berwick Rangers
 Second Round
Feb12  0-0  Clyde v Celtic
Feb24  3-0  Celtic v Clyde
Feb08  6-2  Dundee United v Ayr United
Feb24  2-0  Rangers v Heart of Midlothian
Feb08  1-3  Stranraer v Greenock Morton
Feb08  1-1  East Stirlingshire v St Johnstone
Feb24  3-0  St Johnstone v East Stirlingshire
Feb12  1-1  Airdrieonians v St Mirren
Feb24  1-3  St Mirren v Airdrieonians
Feb25  2-2  Aberdeen v Dunfermline Athletic
Feb26  0-2  Dunfermline Athletic v Aberdeen
Feb08  1-1  Montrose v Kilmarnock
Feb12  4-1  Kilmarnock v Montrose
 Third Round
Mar01  3-2  Celtic v St Johnstone
Mar01  1-0  Rangers v Airdrieonians
Mar01  2-3  Dundee United v Greenock Morton
Mar01  0-0  Aberdeen v Kilmarnock
Mar05  0-3  Kilmarnock v Aberdeen
 Semi-finals
Mar22  4-1  Celtic v Greenock Morton  at Hampden Park
Mar22  1-6  Aberdeen v Rangers  at Celtic Park
 Final
Apr26  4-0  Celtic v Rangers  at Hampden Park