Rangers’ prize for eliminating Premier Sports Cup holders St Mirren is a tantalizing quarter-final tie against Old Firm rivals Celtic.
Derek McInnes secured his first victory as manager with a commanding 5-1 win on Sunday, and his side will now host Celtic.
Stenhousemuir, who shocked Motherwell in extra time, will welcome last season’s Scottish Premiership runners-up Hearts.
Aberdeen travel to Kilmarnock in an all–top-flight clash, while Ross County host Hibernian in the Highlands.
The quarter-finals will take place over the weekend of 12–13 September.
McInnes’ first Old Firm match as Rangers boss had been scheduled for Celtic Park on Sunday 20 September, but this cup tie brings the derby to the other side of the city first.
Kilmarnock became the first team into the last eight after edging Ayrshire rivals Ayr United in a five-goal thriller.
Elsewhere, Aberdeen beat Dundee 3-0 at Pittodrie on Saturday, Ross County defeated Dunfermline 2-1, and Celtic swept past Dundee United 4-0 at Tannadice.