Season 1968-69

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