Season 1999-00

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