Season 1965-66Rangers
 First Preliminary Round
Jan08  6-1  Gala Fairydean v Selkirk
Jan08  2-2  Dumbarton v Peebles Rovers
Jan12  2-3  Peebles Rovers v Dumbarton a.e.t. 2-2
Jan08  1-0  Berwick Rangers v Stenhousemuir
Jan08  1-1  Forfar Athletic v Brechin City
Jan12  1-3  Brechin City v Forfar Athletic
Jan08  1-0  Raith Rovers v Inverness Caledonian
 Second Preliminary Round
Jan22  4-3  Ross County v Forfar Athletic
Jan22  4-5  Gala Fairydean v Montrose
Jan22  1-2  Glasgow University v Dumbarton
Jan22  0-1  Raith Rovers v Alloa Athletic
Jan22  1-0  East Fife v Elgin City
Jan22  0-0  Berwick Rangers v Albion Rovers
Jan26  3-0  Albion Rovers v Berwick Rangers
Jan22  2-2  Arbroath v Cowdenbeath
Jan26  1-1  Cowdenbeath v Arbroath a.e.t. 1-1
Jan31  2-3  Arbroath v Cowdenbeath  at Tannadice Park a.e.t. 2-2
Jan22  1-0  Ayr United v Fraserburgh
 First Round
Feb09  1-0  Cowdenbeath v St Mirren
Feb05  3-0  Queen of the South v Albion Rovers
Feb09  9-1  Dundee v East Fife
Feb09  2-1  Dumbarton v Montrose
Feb09  2-1  Heart of Midlothian v Clyde
Feb05  3-1  Dunfermline Athletic v Partick Thistle
Feb07  0-0  Dundee United v Falkirk
Feb16  1-2  Falkirk v Dundee United a.e.t. 1-1
Feb05  1-1  Greenock Morton v Kilmarnock
Feb09  3-0  Kilmarnock v Greenock Morton
Feb05  5-1  Rangers v Airdrieonians
Feb05  1-3  Hamilton Academical v Aberdeen
Feb05  3-1  Stirling Albion v Queen’s Park
Feb05  4-3  Hibernian v Third Lanark
Feb05  4-0  Celtic v Stranraer
Feb05  1-1  Ayr United v St Johnstone
Feb14  1-0  St Johnstone v Ayr United
Feb10  3-5  Alloa Athletic v Ross County
Feb09  0-0  East Stirlingshire v Motherwell
Feb14  4-1  Motherwell v East Stirlingshire
 Second Round
Feb28  0-2  Ross County v Rangers
Feb21  2-1  Heart of Midlothian v Hibernian
Feb23  0-0  Stirling Albion v Dunfermline Athletic
Feb28  4-1  Dunfermline Athletic v Stirling Albion
Feb23  0-2  Dundee v Celtic
Feb28  3-3  Cowdenbeath v St Johnstone
Mar01  3-0  St Johnstone v Cowdenbeath
Feb23  5-0  Aberdeen v Dundee United
Feb21  5-0  Kilmarnock v Motherwell
Feb23  1-0  Dumbarton v Queen of the South
 Third Round
Mar05  3-3  Heart of Midlothian v Celtic
Mar09  3-1  Celtic v Heart of Midlothian
Mar05  0-3  Dumbarton v Aberdeen
Mar05  1-0  Rangers v St Johnstone
Mar05  2-1  Dunfermline Athletic v Kilmarnock
 Semi-finals
Mar26  0-0  Aberdeen v Rangers  at Hampden Park
Mar29  1-2  Aberdeen v Rangers  at Hampden Park
Mar26  2-0  Celtic v Dunfermline Athletic  at Ibrox Park
 Final
Apr23  0-0  Rangers v Celtic  at Hampden Park
Apr27  1-0  Rangers v Celtic  at Hampden Park