The other ties see SJFA North Superleague side Culter rewarded with a home tie against Berwick Rangers whilst Dunfermline travel to Elgin City.
Two ties will be all-Championship affairs, with Dumbarton taking on Cowdenbeath and Hamilton travelling to face Queen of the South.
The winners of the replay between Edinburgh City and Fraserburgh will face Montrose.
Albion Rovers v Deveronvale / Linlithgow Rose
Alloa Athletic v Inverurie Loco Works
Arbroath v Brechin City
Ayr United v Queen’s Park / Preston Athletic
Clyde v Brora Rangers / Cove Rangers
Culter v Berwick Rangers
Dumbarton v Cowdenbeath
East Stirlingshire v Raith Rovers
Edinburgh City / Fraserburgh v Montrose
Elgin City v Dunfermline Athletic
Forfar Athletic v East Fife
Queen of the South v Hamilton Academical
Rangers v Airdrieonians
Stenhousemuir v Buckie Thistle / Annan Athletic
Stranraer v Auchinleck Talbot
Turiff United v Stirling Albion / Whitehill Welfare
Ties to be played on the weekend of November 2nd and 3rd.