Annagh United’s reward for their historic victory over Glentoran is to host League Cup holders Cliftonville in the last 16 of the competition.
The Reds have won the tournament in each of the last four seasons and recorded a record scoreline for the club when they defeated Lisburn Distillery 11-1 earlier this week.
In other eye-catching ties, Linfield will travel to Ballymena United while Portadown will play host to Crusaders.
Championship side Armagh will host Premiership strugglers Carrick, while Warrenpoint, Knockbreda and HW Welders will face trips to Ards, Coleraine and Glenavon respectively, while Dungannon host Ballinamallard.
Wednesday 12 October, all kick-offs 7.45pm
Annagh v Cliftonville
Ards v Warrenpoint
Armagh v Carrick Rangers
Ballymena v Linfield
Coleraine v Knockbreda
Dungannon v Ballinamallard
Glenavon v HW Welders
Portadown v Crusaders