The all-Premier Division clash is the standout tie of the round. Talbot have won the trophy a record 12 times while Rob Roy have won it twice and been in nine finals, including the last final of the competition played in 2019 when they lost to Beith.
Rossvale will be at home to the winners of the preliminary round tie between Ashfield and Glasgow University, while Petershill are away to Kello Rovers.
Glasgow Perthshire are away to Forth Wanderers in the preliminary round with the winners at home to Lesmahagow.
The full draw is -
Preliminary Round: Hurlford United v Vale of Leven, Glenafton Athletic v Gartcairn Juniors, Troon v Ardeer Thistle, Larkhall Thistle v Cambuslang Rangers, Harthill Royal v Greenock Juniors, Forth Wanderers v Glasgow Perthshire, Whitletts Victoria v Vale of Clyde, Ardrossan Winton Rovers v Arthurlie, Ashfield v Glasgow University, Renfrew v Johnstone Burgh.
1st Round: Rutherglen Glencairn v Finnart Star, Rossvale v Ashfield/Glasgow University, Yoker Athletic v Largs Thistle, Royal Albert v Kilwinning Rangers, Glenafton/Gartcairn v BSC Glasgow, Shotts Bon Accord v Port Glasgow Juniors, Dalry Thistle v St Roch's, Ardrossan Winton Rovers/Arthurlie v Glasgow United, Kello Rovers v Petershill, St Cadoc's v Whitletts Victoria/Vale of Clyde, Benburb v Kilsyth Athletic, Maryhill v Cumnock Juniors, Thorniewood United v Blantyre Victoria, Glenvale v Kilsyth Rangers, Craigmark Burntonians v St Peters, St Anthony's v East Kilbride Thistle.
Bonnyton Thistle v Newmains United, Beith Juniors v Wishaw, Renfrew/Johnstone Burgh v Lanark United, Bellshill Athletic v Irvine Victoria, Darvel v Muirkirk Juniors, Carluke Rovers v Clydebank, Harmony Row v Girvan, Hurlford United/Vale of Leven v Kilbirnie Ladeside. Kirkintilloch Rob Roy v Auchinleck Talbot, Maybole Juniors v Harthill Royal/Greenock Juniors, Larkhall Thistle/Cambuslang Rangers v Drumchapel United, Neilson v Cumbernauld United, Saltcoats Victoria v Irvine Meadow XI, Forth Wanderers/Glasgow Perthshire v Lesmahagow, Lugar Boswell Thistle v Troon/Ardeer Thistle, Pollok v Campbelltown Pupils.
The preliminary round matches are due to be played on Saturday, October 30, with the first round scheduled for Saturday, December 11.