Season 2009-10Dundee United
 First Round
Sep26  3-0  Selkirk v Preston Athletic
Sep26  2-2  Clachnacuddin v Wick Academy
Oct03  2-1  Wick Academy v Clachnacuddin
Sep26  7-0  Auchinleck Talbot v Fort William
Sep26  5-2  Nairn County v Golspie Sutherland
Sep26  0-3  Edinburgh University v Vale of Leithen
Sep26  5-0  Inverurie Loco Works v St Cuthbert Wanderers
Sep26  1-5  Coldstream v Edinburgh City
Sep26  0-2  Brora Rangers v Irvine Meadow XI
Sep26  0-0  Buckie Thistle v Forres Mechanics
Oct03  0-0  Forres Mechanics v Buckie Thistle a.e.t. 0-0 pens 1-4
Sep26  1-1  Whitehill Welfare v Wigtown & Bladnoch
Oct03  0-3  Wigtown & Bladnoch v Whitehill Welfare
Sep26  1-1  Fraserburgh v Bonnyrigg Rose Athletic
Oct03  1-2  Bonnyrigg Rose Athletic v Fraserburgh
Sep26  1-4  Glasgow University v Girvan
Sep26  4-1  Lossiemouth v Newton Stewart
Sep26  1-5  Rothes v Banks O’Dee
Sep26  1-0  Civil Service Strollers v Gala Fairydean
Sep26  0-7  Hawick Royal Albert v Huntly
Sep26  2-4  Dalbeattie Star v Keith
 Second Round
Oct24  1-3  Queen’s Park v Livingston
Oct24  2-4  Nairn County v Elgin City
Oct24  1-4  Fraserburgh v Spartans
Oct24  2-2  Deveronvale v Buckie Thistle
Oct31  1-3  Buckie Thistle v Deveronvale a.e.t. 1-1
Oct24  1-1  Whitehill Welfare v Threave Rovers
Oct31  1-0  Threave Rovers v Whitehill Welfare
Oct24  2-1  Inverurie Loco Works v Stranraer
Oct24  1-3  Vale of Leithen v Keith
Oct24  4-2  Forfar Athletic v East Stirlingshire
Oct24  2-1  Cove Rangers v Annan Athletic
Oct24  0-3  Selkirk v Irvine Meadow XI
Oct24  1-4  Girvan v Wick Academy
Oct24  0-2  Lossiemouth v Albion Rovers
Oct24  5-1  Edinburgh City v Burntisland Shipyard Amateurs
Oct24  0-3  Banks O’Dee v Montrose
Oct24  1-1  Huntly v Auchinleck Talbot
Oct31  4-3  Auchinleck Talbot v Huntly
Oct24  1-2  Civil Service Strollers v Berwick Rangers
 Third Round
Nov28  4-0  Airdrie United v Queen of the South
Nov28  5-1  Ross County v Berwick Rangers
Nov28  1-2  Threave Rovers v Inverurie Loco Works
Nov28  0-1  Deveronvale v Ayr United
Nov28  0-0  Cowdenbeath v Alloa Athletic
Dec08  1-0  Alloa Athletic v Cowdenbeath
Nov28  1-0  Albion Rovers v Elgin City
Nov28  2-1  Stirling Albion v Auchinleck Talbot
Dec09  1-1  Clyde v Livingston
Dec14  7-1  Livingston v Clyde
Nov28  1-0  Irvine Meadow XI v Arbroath
Nov28  3-1  Edinburgh City v Keith
Nov28  4-4  Wick Academy v Brechin City
Dec08  4-2  Brechin City v Wick Academy
Dec05  5-0  Stenhousemuir v Cove Rangers
Nov28  0-0  Greenock Morton v Dumbarton
Dec05  0-1  Dumbarton v Greenock Morton
Nov28  2-1  Montrose v East Fife
Nov28  0-0  Raith Rovers v Peterhead
Dec01  1-4  Peterhead v Raith Rovers
Nov28  0-1  Spartans v Forfar Athletic
 Fourth Round
Jan18  2-0  Inverness Caledonian Thistle v Motherwell
Jan10  3-3  Hamilton Academical v Rangers
Jan19  2-0  Rangers v Hamilton Academical a.e.t. 0-0
Jan19  0-1  Greenock Morton v Celtic
Jan09  3-0  Hibernian v Irvine Meadow XI
Jan09  3-1  St Mirren v Alloa Athletic
Jan25  1-1  Raith Rovers v Airdrie United
Jan27  1-3  Airdrie United v Raith Rovers
Jan09  7-1  Dunfermline Athletic v Stenhousemuir D.A. ineligible player
Jan26  1-2  Stenhousemuir v Dunfermline Athletic a.e.t. 1-1
Jan18  0-3  Forfar Athletic v St Johnstone
Jan20  0-1  Livingston v Dundee
Jan18  0-0  Albion Rovers v Stirling Albion
Jan20  3-1  Stirling Albion v Albion Rovers
Jan09  2-0  Aberdeen v Heart of Midlothian
Jan18  1-3  Edinburgh City v Montrose
Jan09  0-2  Partick Thistle v Dundee United
Jan18  4-0  Ross County v Inverurie Loco Works
Jan18  1-0  Ayr United v Brechin City
Jan18  1-0  Kilmarnock v Falkirk
 Fifth Round
Feb07  2-4  Dunfermline Athletic v Celtic
Feb06  0-1  St Johnstone v Dundee United
Feb06  5-1  Hibernian v Montrose
Feb06  2-1  Dundee v Ayr United
Feb06  1-1  Raith Rovers v Aberdeen
Feb16  0-1  Aberdeen v Raith Rovers
Feb06  3-0  Kilmarnock v Inverness Caledonian Thistle
Feb06  0-0  St Mirren v Rangers
Feb17  1-0  Rangers v St Mirren
Feb06  9-0  Ross County v Stirling Albion
 Sixth Round
Mar14  3-3  Rangers v Dundee United
Mar24  1-0  Dundee United v Rangers
Mar13  2-2  Hibernian v Ross County
Mar23  2-1  Ross County v Hibernian
Mar13  0-3  Kilmarnock v Celtic
Mar13  1-2  Dundee v Raith Rovers
 Semi-finals
Apr10  0-2  Celtic v Ross County  at Hampden Park
Apr11  2-0  Dundee United v Raith Rovers  at Hampden Park
 Final
May15  0-3  Ross County v Dundee United  at Hampden Park