Rangers will face holders Falkirk in the second round of the Ramsdens Cup following the draw at Parkhead Forge.
Steven Pressley's men will host the Third Division club after newco Rangers won their first competitive match on Sunday against Brechin City.
Falkirk, who just missed out on promotion to the top flight last term when they also progressed to the semi-final of the Co-operative Insurance Cup, will provide a stern test for Ally McCoist's team.
The other standout ties involve Cowdenbeath playing neighbours East Fife and a Glasgow derby between Queen's Park and Partick Thistle - the matches will take place on Tuesday 14th and Wednesday 15th August.
Ramsdens Cup second round draw:
Cowdenbeath v East Fife
Raith Rovers v Montrose
Arbroath v Forfar
Falkirk v Rangers
Annan v Stenhousemuir
Queen's Park v Partick
Morton v Queen of the South
East Stirlingshire v Airdrie Utd