Season 1998-99Rangers
 First Round
Dec05  1-2  Arbroath v Partick Thistle
Dec05  1-1  Dumbarton v Livingston
Dec08  3-0  Livingston v Dumbarton
Dec05  2-0  Queen’s Park v Berwick Rangers
Dec05  1-1  Stenhousemuir v Alloa Athletic
Dec12  0-2  Alloa Athletic v Stenhousemuir
 Second Round
Jan18  1-1  Queen’s Park v Clachnacuddin
Jan23  2-3  Clachnacuddin v Queen’s Park
Jan09  1-3  Queen of the South v Ross County
Jan02  0-3  Civil Service Strollers v Albion Rovers
Jan02  1-2  Dalbeattie Star v East Stirlingshire
Jan02  2-2  Forfar Athletic v East Fife
Jan09  0-1  East Fife v Forfar Athletic
Jan02  3-0  Huntly v Peterhead
Jan02  1-2  Inverness Caledonian Thistle v Livingston
Jan02  0-0  Keith v Brechin City
Jan09  3-1  Brechin City v Keith
Jan02  0-0  Montrose v Stirling Albion
Jan18  2-1  Stirling Albion v Montrose
Jan02  5-2  Partick Thistle v Cowdenbeath
Jan02  1-1  Spartans v Clyde
Jan06  5-0  Clyde v Spartans
Jan02  1-1  Whitehill Welfare v Stenhousemuir
Jan09  2-0  Stenhousemuir v Whitehill Welfare
 Third Round
Feb03  1-1  Clydebank v Ross County
Feb15  2-3  Ross County v Clydebank
Feb02  0-0  Queen’s Park v Dundee United
Feb09  1-0  Dundee United v Queen’s Park
Jan24  3-1  Motherwell v Heart of Midlothian
Jan23  0-1  Aberdeen v Livingston
Jan23  3-0  Ayr United v Kilmarnock
Jan23  1-1  Brechin City v Albion Rovers
Feb02  3-1  Albion Rovers v Brechin City
Jan23  3-1  Celtic v Airdrieonians
Jan23  3-0  Falkirk v Huntly
Jan23  1-1  Hibernian v Stirling Albion
Feb02  2-1  Stirling Albion v Hibernian
Jan23  2-1  Greenock Morton v Dundee
Jan23  1-2  Partick Thistle v Dunfermline Athletic
Jan23  0-4  Raith Rovers v Clyde
Jan23  2-0  Rangers v Stenhousemuir
Jan23  1-0  St Johnstone v Forfar Athletic
Jan23  1-1  St Mirren v Hamilton Academical
Feb02  1-0  Hamilton Academical v St Mirren
Jan23  1-0  Stranraer v East Stirlingshire
 Fourth Round
Feb13  1-0  Ayr United v Albion Rovers
Mar03  2-2  Clydebank v Dundee United
Mar06  3-0  Dundee United v Clydebank
Feb13  2-0  Motherwell v Stirling Albion
Feb13  6-1  Greenock Morton v Clyde
Feb14  0-6  Hamilton Academical v Rangers
Feb13  1-2  Stranraer v Falkirk
Feb13  1-3  Livingston v St Johnstone
Feb13  4-0  Celtic v Dunfermline Athletic
 Fifth Round
Mar13  0-0  Ayr United v Dundee United
Mar16  2-1  Dundee United v Ayr United
Mar08  0-3  Greenock Morton v Celtic
Mar07  2-1  Rangers v Falkirk
Mar06  0-2  Motherwell v St Johnstone
 Semi-finals
Apr10  2-0  Celtic v Dundee United
Apr11  0-4  St Johnstone v Rangers
 Final
Mar29  1-0  Rangers v Celtic  at Hampden Park