Rangers will visit The Falkirk Stadium on cup duty for the second season in a row and will face holders Falkirk.
Ally McCoist’s side fell to a 3-2 defeat thanks to a last-gasp free-kick by Mark Millar in September last year.
Falkirk went on to reach the semi-finals of the Communities League Cup - but also won the Ramsdens tournament later in the season.
Steven Pressley told The Falkirk Herald the draw was one that would whet supporters’ appetites.
“It’s another game for the supporters, and the players to look forward to, but we are the cup holders and it is important to us to defend our trophy.”
The tie will likely be played on August 15 as The Falkirk Stadium is being used on August 14 for a Scotland international under-19s match with Germany.
Rangers saw off Brechin after extra-time yesterday 2-1, and Falkirk beat Stirling Albion 3-0 on Saturday.
Stenhousemuir and East Stirlingshire also progressed and the Warriors will face another long trip after winning at Stranraer, after being drawn at last year’s semi-finalists Annan Athletic.
The Shire welcome Airdrie United to Ochilview.