Hibernian will face Dundee again in the Betfred Cup knockout round - after beating them 4-1 in the group stages at Easter Road.
Jack Ross and James McPake will go head to head again after the men in green and white came out on top of their encounter in Leith on Sunday minutes before the draw was made.
Meanwhile Hearts face Alloa Athletic in one of two all Championship ties set to be played in the knockout round.
Robbie Neilson's men went through the group stages unbeaten, but will face a tough test against the Wasps, who finished second to Livingston in Group H.
Elsewhere, Rangers go to Falkirk, Celtic host Ross County and Motherwell face St Johnstone.
Arbroath face Dunfermline at Gayfield and Aberdeen go to St Mirren while Livingston face Ayr United - who topped a group containing Premiership Hamilton Academical.
The ties will be played on the weekend of 28/29 November:
Draw in full:
Celtic v Ross County
Falkirk v Rangers
Livingston v Ayr United
St Mirren v Aberdeen
Hibernian v Dundee
Arbroath v Dunfermline
Motherwell v St Johnstone
Alloa Athletic v Hearts
