Season 1949-50Rangers
 First Round
Jan28  2-3  Clachnacuddin v Stenhousemuir
Jan28  1-1  Kilmarnock v Stirling Albion
Feb01  3-1  Stirling Albion v Kilmarnock
Jan28  1-3  Stranraer v Falkirk
Jan28  0-1  Alloa Athletic v Albion Rovers
Jan28  2-4  Motherwell v Rangers
Jan28  4-0  Dundee United v Ayr United
Jan28  2-1  Third Lanark v Arbroath
Jan28  1-2  St Mirren v Aberdeen
Jan28  5-3  Dunfermline Athletic v Forfar Athletic
Jan28  0-1  Hibernian v Partick Thistle
Jan28  7-3  St Johnstone v Leith Athletic
Jan28  3-0  Raith Rovers v Airdrieonians
Feb01  1-0  Cowdenbeath v Hamilton Academical
Jan28  1-0  Dumbarton v Queen’s Park
Jan28  0-3  Ross County v Greenock Morton
Jan28  0-1  Inverness Caledonian v Queen of the South
Jan28  1-1  Heart of Midlothian v Dundee
Feb06  1-2  Dundee v Heart of Midlothian a.e.t. 1-1
Jan28  4-3  Clyde v Newton Stewart
Jan28  0-3  Brechin City v Celtic
Jan28  4-0  East Fife v Fraserburgh
 Second Round
Feb11  2-2  Stirling Albion v Dumbarton
Feb15  1-1  Dumbarton v Stirling Albion a.e.t. 1-1
Feb22  6-3  Stirling Albion v Dumbarton  at Ibrox Park
Feb11  4-2  Raith Rovers v Clyde
Feb11  1-1  Queen of the South v Greenock Morton
Feb15  0-1  Greenock Morton v Queen of the South
Feb11  2-2  Stenhousemuir v St Johnstone
Feb15  2-4  St Johnstone v Stenhousemuir
Feb11  3-1  Aberdeen v Heart of Midlothian
Feb14  5-0  Partick Thistle v Dundee United
Feb15  1-1  Third Lanark v Celtic
Feb20  4-1  Celtic v Third Lanark
Feb11  8-0  Rangers v Cowdenbeath
Feb11  2-3  Falkirk v East Fife
Feb15  1-2  Albion Rovers v Dunfermline Athletic
 Third Round
Feb25  1-4  Dunfermline Athletic v Stenhousemuir
Feb25  0-1  Celtic v Aberdeen
       bye  Raith Rovers, Rangers, East Fife, Partick Thistle,
            Stirling Albion, Queen of the South
 Fourth Round
Mar11  5-1  Partick Thistle v Stirling Albion
Mar11  1-1  Rangers v Raith Rovers
Mar15  1-1  Raith Rovers v Rangers a.e.t. 1-1
Mar27  2-0  Rangers v Raith Rovers  at Ibrox Park
Mar11  0-3  Stenhousemuir v East Fife
Mar11  3-3  Queen of the South v Aberdeen
Mar15  1-2  Aberdeen v Queen of the South
 Semi-finals
Apr01  1-1  Queen of the South v Rangers  at Hampden Park
Apr05  0-3  Queen of the South v Rangers  at Hampden Park
Apr01  1-2  Partick Thistle v East Fife  at Ibrox Park
 Final
Apr22  3-0  Rangers v East Fife  at Hampden Park