Season 2008-09Rangers
 First Round
Sep27  1-3  Rothes v Buckie Thistle
Sep27  0-3  Golspie Sutherland v Threave Rovers
Sep27 10-0  Banks O’Dee v Fort William
Sep27  3-1  Lochee United v Bathgate Thistle
Sep27  1-1  Selkirk v Coldstream
Oct04  2-2  Coldstream v Selkirk a.e.t. 2-2 pens 2-3
Sep27  0-3  St Cuthbert Wanderers v Wick Academy
Sep27  6-3  Fraserburgh v Hawick Royal Albert
Sep27  1-1  Newton Stewart v Brora Rangers
Oct04  2-1  Brora Rangers v Newton Stewart a.e.t. 1-1
Sep27  1-0  Huntly v Girvan
Sep27  1-1  Pollok v Spartans
Oct04  1-0  Spartans v Pollok
Sep27  2-0  Edinburgh City v Nairn County
Sep27  5-2  Inverurie Loco Works v Deveronvale
Sep27  5-1  Dalbeattie Star v Lossiemouth
Sep27  1-2  Edinburgh University v Civil Service Strollers
Sep27  3-1  Preston Athletic v Gala Fairydean
Sep27  2-2  Wigtown & Bladnoch v Forres Mechanics
Oct04  2-0  Forres Mechanics v Wigtown & Bladnoch
Sep27  4-0  Clachnacuddin v Burntisland Shipyard Amateurs
Sep27  0-1  Glasgow University v Vale of Leithen
 Second Round
Oct25  1-0  Clachnacuddin v Crichton
Oct25  0-0  Edinburgh City v Wick Academy
Nov01  1-4  Wick Academy v Edinburgh City
Oct25  1-0  Cove Rangers v Whitehill Welfare
Oct25  6-0  Dalbeattie Star v Selkirk
Oct25  2-0  Montrose v Huntly
Oct26  4-2  East Stirlingshire v Preston Athletic
Oct25  0-1  Fraserburgh v Dumbarton
Oct25  1-2  Berwick Rangers v Albion Rovers
Nov01  0-1  Civil Service Strollers v Vale of Leithen
Oct25  5-1  Inverurie Loco Works v Banks O’Dee
Oct25  5-0  Stenhousemuir v Threave Rovers
Nov01  1-2  Annan Athletic v Spartans
Oct25  1-3  Brora Rangers v Forfar Athletic
Oct25  3-0  Lochee United v Buckie Thistle
Oct25  1-2  Cowdenbeath v Elgin City
Oct25  1-1  Forres Mechanics v Keith
Nov01  1-1  Keith v Forres Mechanics a.e.t. 1-1 pens 0-3
 Third Round
Nov29  2-3  Stirling Albion v Partick Thistle
Dec15  2-0  Forfar Athletic v Stranraer
Dec17  1-1  Lochee United v Ayr United
Dec23  3-1  Ayr United v Lochee United
Dec06  2-2  Forres Mechanics v Dalbeattie Star
Dec15  2-4  Dalbeattie Star v Forres Mechanics a.e.t. 1-1
Dec13  4-0  Inverurie Loco Works v Vale of Leithen
Dec06  2-1  Elgin City v Spartans E.C. ineligible player
Dec15  1-2  Elgin City v Spartans S. £2500 fine for ineligible player in 1st match
Nov29  2-1  East Stirlingshire v Livingston
Dec08  0-3  Edinburgh City v Brechin City
Nov29  1-2  Albion Rovers v Queen’s Park
Nov29  2-0  East Fife v Arbroath
Nov29  2-1  Peterhead v Greenock Morton
Nov29  2-0  Clyde v Montrose
Nov29  3-0  Airdrie United v Cove Rangers
Nov29  0-0  Raith Rovers v Alloa Athletic
Dec09  2-1  Alloa Athletic v Raith Rovers
Nov29  0-5  Clachnacuddin v Stenhousemuir
Nov29  2-2  Ross County v Dumbarton
Dec15  1-2  Dumbarton v Ross County
 Fourth Round
Jan10  2-2  Peterhead v Queen’s Park
Jan20  1-0  Queen’s Park v Peterhead
Jan13  0-2  St Johnstone v Rangers
Jan10  1-2  Alloa Athletic v Aberdeen
Jan10  4-2  Falkirk v Queen of the South
Jan10  2-1  Airdrie United v Spartans
Feb02  0-3  Inverurie Loco Works v Motherwell
Jan10  0-1  Ross County v Hamilton Academical
Jan13  6-1  Forfar Athletic v Forres Mechanics
Jan10  3-0  Inverness Caledonian Thistle v Partick Thistle
Jan10  2-1  Celtic v Dundee
Jan11  0-4  East Stirlingshire v Dundee United
Jan10  0-1  Stenhousemuir v East Fife
Jan11  0-2  Hibernian v Heart of Midlothian
Jan10  2-2  Ayr United v Kilmarnock
Jan22  3-1  Kilmarnock v Ayr United
Jan10  2-0  Dunfermline Athletic v Clyde
Jan13  1-3  Brechin City v St Mirren
 Fifth Round
Feb18  0-4  Forfar Athletic v Rangers
Feb17  1-2  Airdrie United v Dunfermline Athletic
Feb07  0-1  Heart of Midlothian v Falkirk
Feb07  1-1  Motherwell v St Mirren
Feb19  1-0  St Mirren v Motherwell
Feb17  5-0  Aberdeen v East Fife
Feb07  2-1  Celtic v Queen’s Park
Feb07  2-1  Hamilton Academical v Dundee United
Feb07  2-0  Inverness Caledonian Thistle v Kilmarnock
 Sixth Round
Mar07  1-0  St Mirren v Celtic
Mar07  1-1  Dunfermline Athletic v Aberdeen
Mar18  0-0  Aberdeen v Dunfermline Athletic a.e.t. 0-0 pens 2-4
Mar07  0-1  Inverness Caledonian Thistle v Falkirk
Mar08  5-1  Rangers v Hamilton Academical
 Semi-finals
Apr25  3-0  Rangers v St Mirren  at Hampden Park
Apr26  2-0  Falkirk v Dunfermline Athletic  at Hampden Park
 Final
May30  1-0  Rangers v Falkirk  at Hampden Park