Holders St Patrick's Athletic will host Bluebell United, Wexford take on neighbours Waterford, while Athlone Town meet Longford Town in the midlands derby.
All First Round ties will be decided on the night with extra-time and penalties to be played if required.
Pool 1
Cobh Ramblers v Avondale United, St Colman's Park, KO 19:45
Wexford v Waterford, Ferrycarrig Park, KO 20:00
Byes: Cork City, Limerick
Pool 2
Galway United v Mayo League, Eamonn Deacy Park, KO 19:45
Finn Harps v Cockhill Celtic, Finn Park, KO 20:00
Byes: Derry City, Sligo Rovers
Pool 3
Drogheda United v Bray Wanderers, United Park, KO 19:45
St Patrick's Athletic v Bluebell United, Richmond Park. KO 19:45
Byes: Dundalk, UCD
Pool 4
Athlone Town v Longford Town, Athlone Town Stadium, KO 19:45
Bohemians v Cabinteely, Dalymount Park, KO 19:45
Byes: Shamrock Rovers, Shelbourne