Season 1998-99Rangers
 Qualifying Cup North First Round
Aug29  0-2  Deveronvale v Rothes
 Qualifying Cup North Second Round
Sep19  7-1  Brora Rangers v Lossiemouth
Sep19  0-1  Buckie Thistle v Forres Mechanics
Sep19  3-1  Cove Rangers v Elgin City
Sep19  0-3  Golspie Sutherland v Rothes
Sep19  3-0  Huntly v Fort William
Sep19  0-7  Nairn County v Keith
Sep19  1-1  Peterhead v Fraserburgh
Sep26  1-3  Fraserburgh v Peterhead
Sep19  1-1  Wick Academy v Clachnacuddin
Sep26  2-0  Clachnacuddin v Wick Academy
 Qualifying Cup North Third Round
Oct03  1-2  Cove Rangers v Clachnacuddin
Oct03  4-1  Huntly v Forres Mechanics
Oct03  1-1  Keith v Rothes
Oct10  1-4  Rothes v Keith
Oct03  1-0  Peterhead v Brora Rangers
 Qualifying Cup North Semi-finals – teams qualified for the cup proper
Oct17  3-2  Clachnacuddin v Huntly
Oct28  2-1  Keith v Peterhead
 Qualifying Cup North Final
Nov07  3-1  Clachnacuddin v Keith  at Borough Briggs
 First Round
Dec05  1-2  Arbroath v Partick Thistle
Dec05  1-1  Stenhousemuir v Alloa Athletic
Dec12  0-2  Alloa Athletic v Stenhousemuir
Dec05  1-1  Dumbarton v Livingston
Dec08  3-0  Livingston v Dumbarton
Dec05  2-0  Queen’s Park v Berwick Rangers
 Second Round
Jan09  1-3  Queen of the South v Ross County
Jan02  0-3  Civil Service Strollers v Albion Rovers
Jan02  0-0  Montrose v Stirling Albion
Jan18  2-1  Stirling Albion v Montrose
Jan02  1-1  Whitehill Welfare v Stenhousemuir
Jan09  2-0  Stenhousemuir v Whitehill Welfare
Jan02  0-0  Keith v Brechin City
Jan09  3-1  Brechin City v Keith
Jan02  1-2  Dalbeattie Star v East Stirlingshire
Jan18  1-1  Queen’s Park v Clachnacuddin
Jan23  2-3  Clachnacuddin v Queen’s Park
Jan02  1-2  Inverness Caledonian Thistle v Livingston
Jan02  3-0  Huntly v Peterhead
Jan02  5-2  Partick Thistle v Cowdenbeath
Jan02  1-1  Spartans v Clyde
Jan06  5-0  Clyde v Spartans
Jan02  2-2  Forfar Athletic v East Fife
Jan09  0-1  East Fife v Forfar Athletic
 Third Round
Feb02  0-0  Queen’s Park v Dundee United
Feb09  1-0  Dundee United v Queen’s Park
Jan23  2-1  Greenock Morton v Dundee
Jan23  3-0  Ayr United v Kilmarnock
Jan23  1-0  Stranraer v East Stirlingshire
Jan23  3-0  Falkirk v Huntly
Jan23  1-1  Brechin City v Albion Rovers
Feb02  3-1  Albion Rovers v Brechin City
Jan23  1-1  Hibernian v Stirling Albion
Feb02  2-1  Stirling Albion v Hibernian
Jan24  3-1  Motherwell v Heart of Midlothian
Jan23  1-2  Partick Thistle v Dunfermline Athletic
Jan23  1-0  St Johnstone v Forfar Athletic
Jan23  0-4  Raith Rovers v Clyde
Jan23  1-1  St Mirren v Hamilton Academical
Feb02  1-0  Hamilton Academical v St Mirren
Jan23  3-1  Celtic v Airdrieonians
Jan23  2-0  Rangers v Stenhousemuir
Feb03  1-1  Clydebank v Ross County
Feb15  2-3  Ross County v Clydebank
Jan23  0-1  Aberdeen v Livingston
 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
Mar06  0-2  Motherwell v St Johnstone
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
 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