Season 1999-00Rangers
 First Round
Dec11  1-2  Hamilton Academical v Clyde
Dec11  0-1  Huntly v East Stirlingshire
Dec11  2-2  Ross County v Forfar Athletic
Jan03  0-0  Forfar Athletic v Ross County a.e.t. 0-0 pens 4-2
Dec27  1-7  Threave Rovers v Stenhousemuir
 Second Round
Jan08  0-0  Albion Rovers v Dalbeattie Star
Jan19  1-5  Dalbeattie Star v Albion Rovers
Jan08  0-0  Arbroath v Fraserburgh
Jan15  1-3  Fraserburgh v Arbroath
Jan08  2-2  Brechin City v Annan Athletic
Jan15  2-3  Annan Athletic v Brechin City a.e.t. 2-2
Jan08  2-3  Cowdenbeath v Clyde
Jan08  0-2  Dumbarton v Stenhousemuir
Jan08  1-3  Montrose v Queen of the South
Jan08  2-1  Partick Thistle v East Stirlingshire
Jan08  2-1  Peterhead v Forfar Athletic
Jan08  1-2  Queen’s Park v Berwick Rangers
Jan08  2-1  Stirling Albion v East Fife
Jan08  1-0  Stranraer v Clachnacuddin
Jan08  2-2  Whitehill Welfare v Alloa Athletic
Jan29  2-0  Alloa Athletic v Whitehill Welfare
 Third Round
Jan29  3-2  Heart of Midlothian v Stenhousemuir
Jan29  1-1  St Mirren v Aberdeen
Feb08  2-0  Aberdeen v St Mirren
Jan29  1-2  Albion Rovers v Partick Thistle
Jan30  0-2  St Johnstone v Rangers
Feb08  1-3  Celtic v Inverness Caledonian Thistle
Jan29  3-1  Falkirk v Peterhead
Feb01  1-1  Arbroath v Motherwell
Feb19  2-0  Motherwell v Arbroath
Jan29  0-7  Queen of the South v Livingston
Jan29  3-1  Clyde v Raith Rovers
Jan29  1-2  Stranraer v Berwick Rangers
Jan29  1-0  Clydebank v Stirling Albion
Jan29  4-1  Hibernian v Dunfermline Athletic
Feb05  0-0  Kilmarnock v Alloa Athletic
Feb09  1-0  Alloa Athletic v Kilmarnock
Jan30  1-1  Greenock Morton v Brechin City
Feb08  0-0  Brechin City v Greenock Morton a.e.t. 0-0 pens 3-4
Jan30  4-1  Dundee United v Airdrieonians
Jan29  0-0  Dundee v Ayr United
Feb15  1-1  Ayr United v Dundee a.e.t. 0-0 pens 7-6
 Fourth Round
Feb19  2-2  Alloa Athletic v Dundee United
Feb22  4-0  Dundee United v Alloa Athletic
Feb19  0-0  Berwick Rangers v Falkirk
Feb29  3-0  Falkirk v Berwick Rangers
Feb19  0-2  Clyde v Heart of Midlothian
Feb19  1-1  Hibernian v Clydebank
Feb29  0-3  Clydebank v Hibernian
Feb19  0-1  Greenock Morton v Rangers
Feb20  1-1  Inverness Caledonian Thistle v Aberdeen
Feb29  1-0  Aberdeen v Inverness Caledonian Thistle
Feb26  3-4  Motherwell v Ayr United
Feb19  2-1  Partick Thistle v Livingston
 Fifth Round
Mar11  2-0  Ayr United v Partick Thistle
Mar12  4-1  Rangers v Heart of Midlothian
Mar11  3-1  Hibernian v Falkirk
Mar12  0-1  Dundee United v Aberdeen
 Semi-finals
Apr08  0-7  Ayr United v Rangers  at Hampden Park
Apr09  1-2  Hibernian v Aberdeen  at Hampden Park
 Final
Mar27  0-4  Aberdeen v Rangers  at Hampden Park