Season 1955-56Heart of Midlothian
 First Round
Sep10  3-1  Fraserburgh v Aberdeen University
Sep10  2-2  Tarff Rovers v Girvan Amateurs
Sep17  0-1  Girvan Amateurs v Tarff Rovers
Sep10  7-0  Lossiemouth v Wick Academy
Sep10  3-2  Forres Mechanics v Glasgow University
Sep10  2-1  Buckie Thistle v Rothes
Sep10  3-5  Newton Stewart v Peebles Rovers
Sep10  2-1  Gala Fairydean v Peterhead
Sep10  3-1  St Cuthbert Wanderers v Vale of Atholl
Sep10  3-2  Selkirk v Burntisland Shipyard Amateurs
Sep10  2-5  Babcock & Wilcox v Clachnacuddin
Sep10  4-2  Huntly v Civil Service Strollers
Sep10  4-2  Ross County v Coldstream
Sep10  3-0  Duns v Deveronvale
Sep10  2-2  Murrayfield Amateurs v Shawfield Amateurs
Sep17  2-1  Shawfield Amateurs v Murrayfield Amateurs
Sep10  1-2  Nairn County v Inverness Caledonian
Sep10  5-1  Eyemouth United v Brora Rangers
Sep10  0-7  Wigtown & Bladnoch v Keith
Sep10  1-9  Chirnside United v Elgin City
Sep10  0-7  Edinburgh University v Inverness Thistle
Sep10  4-1  Whithorn v Vale of Leithen protested – pitch length short by 2 yds.
Sep17  7-0  Whithorn v Vale of Leithen
       bye  Berwick Rangers, Dumbarton, East Stirlingshire,
            Montrose, Stranraer
 Second Round
Sep24  2-3  Whithorn v Selkirk
Sep24  3-1  Lossiemouth v Duns
Sep24  3-2  Ross County v Tarff Rovers
Sep17  5-1  Peebles Rovers v Eyemouth United
Sep24  6-2  Gala Fairydean v Shawfield Amateurs
Sep24  5-2  Inverness Thistle v Buckie Thistle
Sep24  3-0  Clachnacuddin v St Cuthbert Wanderers
Sep24  2-4  Huntly v Forres Mechanics
Sep24  2-0  Keith v Elgin City
       bye  Berwick Rangers, Dumbarton, East Stirlingshire,
            Montrose, Stranraer, Inverness Caledonian,
            Fraserburgh
 Third Round
Oct08  4-5  Gala Fairydean v Montrose
Oct08  2-3  Ross County v Stranraer
Oct08  1-1  Inverness Thistle v Peebles Rovers
Oct15  2-1  Peebles Rovers v Inverness Thistle
Oct08  2-4  Keith v East Stirlingshire
Oct08  1-0  Lossiemouth v Selkirk
Oct08  2-4  Forres Mechanics v Clachnacuddin
Oct08  5-3  Dumbarton v Inverness Caledonian
Oct08  3-0  Berwick Rangers v Fraserburgh
 Fourth Round
Oct22  6-0  Cowdenbeath v Montrose
Oct22  1-1  Brechin City v Peebles Rovers
Oct29  4-4  Peebles Rovers v Brechin City a.e.t. 3-3
Nov02  0-0  Brechin City v Peebles Rovers  at Easter Road a.e.t. 0-0
Nov16  6-2  Brechin City v Peebles Rovers  at Tannadice Park
Oct22  5-2  Greenock Morton v Clachnacuddin
Oct22  0-2  East Stirlingshire v Arbroath
Oct22  5-1  Berwick Rangers v Lossiemouth
Oct22  4-1  Dundee United v Dumbarton
Oct22  5-2  Forfar Athletic v Stranraer
Oct22  1-1  Albion Rovers v Alloa Athletic
Oct29  4-0  Alloa Athletic v Albion Rovers
 Fifth Round
Feb08  1-3  East Fife v Stenhousemuir
Feb04  3-1  Queen of the South v Cowdenbeath
Feb04  2-2  Dundee United v Dundee
Feb08  3-0  Dundee v Dundee United
Feb04  7-1  Airdrieonians v Hamilton Academical
Feb04  3-0  Heart of Midlothian v Forfar Athletic
Feb08  0-2  Motherwell v Queen’s Park
Feb04  6-0  St Mirren v Third Lanark
Feb04  1-1  Brechin City v Arbroath
Feb08  2-3  Arbroath v Brechin City
Feb08  5-0  Clyde v Dunfermline Athletic
Feb04  2-1  Stirling Albion v St Johnstone
Feb04  2-1  Rangers v Aberdeen
Feb04  0-3  Falkirk v Kilmarnock
Feb04  2-0  Partick Thistle v Alloa Athletic
Feb04  0-2  Greenock Morton v Celtic
Feb04  5-2  Ayr United v Berwick Rangers
Feb08  1-1  Hibernian v Raith Rovers
Feb13  3-1  Raith Rovers v Hibernian
 Sixth Round
Feb18  2-2  Kilmarnock v Queen of the South
Feb22  2-0  Queen of the South v Kilmarnock
Feb18  0-1  Stenhousemuir v Clyde
Feb18  4-4  Airdrieonians v St Mirren
Feb21  1-3  St Mirren v Airdrieonians
Feb18  0-1  Dundee v Rangers
Feb18  3-1  Partick Thistle v Brechin City
Feb18  0-3  Ayr United v Celtic
Feb18  5-0  Heart of Midlothian v Stirling Albion
Feb18  2-2  Raith Rovers v Queen’s Park
Feb22  1-2  Queen’s Park v Raith Rovers a.e.t. 1-1
 Seventh Round
Mar03  2-4  Queen of the South v Clyde
Mar03  2-1  Celtic v Airdrieonians
Mar03  4-0  Heart of Midlothian v Rangers
Mar03  2-1  Raith Rovers v Partick Thistle
 Semi-finals
Mar24  0-0  Heart of Midlothian v Raith Rovers  at Easter Road
Mar28  3-0  Heart of Midlothian v Raith Rovers  at Easter Road
Mar24  1-2  Clyde v Celtic  at Hampden Park
 Final
Apr21  3-1  Heart of Midlothian v Celtic  at Hampden Park