Season 2019-20TBD
 First Preliminary Round
Aug17  5-0  Lothian Thistle Hutchison Vale v Wigtown & Bladnoch  at Albyn Park
Aug10  2-1  Linlithgow Rose v Preston Athletic
Aug10  1-7  St Cuthbert Wanderers v Girvan
Aug10  2-0  Broxburn Athletic v Tynecastle
Aug10  5-0  Banks O’Dee v Glasgow University
Aug10  2-0  Hill of Beath Hawthorn v Blackburn United
Aug10  1-6  EastHouses Lily Miners Welfare v Penicuik Athletic
Aug18  0-4  Colville Park v Whitehill Welfare  at New Tinto Park
Aug10  2-2  Dundonald Bluebell v Auchinleck Talbot
Aug17  6-1  Auchinleck Talbot v Dundonald Bluebell
Aug10  1-0  Camelon Juniors v Newton Stewart
Aug10  1-9  Coldstream v Jeanfield Swifts
Aug10  1-6  Hawick Royal Albert United v Threave Rovers
Aug10  7-0  Lochee United v Burntisland Shipyard
       bye  Golspie Sutherland
 Second Preliminary Round
Sep07  2-5  Jeanfield Swifts v Linlithgow Rose
Aug31  0-1  Girvan v Broxburn Athletic
Aug31  2-0  Banks O’Dee v Golspie Sutherland
Aug31  0-2  Threave Rovers v Hill of Beath Hawthorn
Aug31  5-2  Lochee United v Lothian Thistle Hutchison Vale
Aug31  0-1  Whitehill Welfare v Penicuik Athletic
Aug31  0-2  Camelon Juniors v Auchinleck Talbot
 First Round
Sep21  3-2  Inverurie Loco Works v Wick Academy
Sep21  3-2  Broxburn Athletic v East Stirlingshire
Sep21  5-0  Fort William v Vale of Leithen
Sep21  1-4  Forres Mechanics v Banks O’Dee
Sep21  2-1  Strathspey Thistle v Lossiemouth
Sep20  0-3  Kelty Hearts v Auchinleck Talbot
Sep21  4-1  Buckie Thistle v Civil Service Strollers
Sep21  0-1  Fraserburgh v Bonnyrigg Rose Athletic
Sep21  0-0  Nairn County v Clachnacuddin
Sep28  2-1  Clachnacuddin v Nairn County
Sep21  1-0  Linlithgow Rose v Huntly
Sep21  1-3  Edinburgh University v Lochee United
Sep21  1-5  Cumbernauld Colts v Penicuik Athletic
Sep21  1-0  Gretna 2008 v Hill of Beath Hawthorn
Sep21  1-3  Dalbeattie Star v Gala Fairydean Rovers
Sep21  1-1  Spartans v Deveronvale
Sep30  1-2  Deveronvale v Spartans
Sep21  1-5  Turriff United v Formartine United
Sep21  2-3  Keith v University of Stirling
Sep21  3-4  Caledonian Braves v Rothes  at Bothwellhaugh
 Second Round
Oct20  0-2  University of Stirling v Linlithgow Rose
Oct19  1-1  Albion Rovers v Fort William
Oct26  0-5  Fort William v Albion Rovers
Oct19  3-1  East Kilbride v Gretna 2008
Oct18  3-1  Edinburgh City v Banks O’Dee
Oct19  1-1  Cowdenbeath v Broxburn Athletic
Oct26  3-0  Broxburn Athletic v Cowdenbeath
Oct19  0-7  Clachnacuddin v Brora Rangers
Oct19  1-3  Rothes v Inverurie Loco Works
Oct19  0-2  Spartans v Queen’s Park
Oct19  3-1  Elgin City v Berwick Rangers
Oct19  2-2  Formartine United v Gala Fairydean Rovers
Oct26  1-2  Gala Fairydean Rovers v Formartine United
Oct26  3-0  Penicuik Athletic v Stenhousemuir
Oct19  2-2  Annan Athletic v Brechin City
Oct26  0-2  Brechin City v Annan Athletic
Oct19  1-1  Lochee United v BSC Glasgow
Oct27  2-1  BSC Glasgow v Lochee United
Oct19  1-0  Auchinleck Talbot v Cove Rangers
Oct18  2-0  Bonnyrigg Rose Athletic v Buckie Thistle
Oct19  2-0  Stirling Albion v Strathspey Thistle
 Third Round
Nov23   –   Auchinleck Talbot v Arbroath
Nov23   –   Stranraer v Dunfermline Athletic
Nov23   –   Dumbarton v Forfar Athletic
Nov23   –   Raith Rovers v Peterhead
Nov23   –   Elgin City v Alloa Athletic
Nov23   –   Greenock Morton v Brora Rangers
Nov23   –   Formartine United v East Kilbride
Nov23   –   Partick Thistle v Penicuik Athletic
Nov23   –   Albion Rovers v Airdrieonians
Nov23   –   Queen of the South v Queen’s Park
Nov23   –   Edinburgh City v Annan Athletic
Nov23   –   Stirling Albion v Clyde
Nov23   –   East Fife v BSC Glasgow
Nov22   –   Linlithgow Rose v Falkirk
Nov23   –   Inverurie Loco Works v Broxburn Athletic
Nov23   –   Bonnyrigg Rose Athletic v Montrose