Cork City’s reward for knocking out Sligo Rovers in the FAI Cup on Saturday is a second-round tie against League of Ireland joint-leaders St Patrick’s Athletic at Turner’s Cross.
Elsewhere there’s a big Dublin derby between Bohemians and Shamrock Rovers and a north-west derby, with Finn Harps hosting Derry City.
Holders Dundalk will host St Mochta’s, while Darren Murphy’s Cobh Ramblers face a trip to take on Leinster Senior League outfit Maynooth University Town.
All eight of the last-16 ties are to be played on the weekend of August 29.
Waterford v Kilnamanagh; Dundalk v St Mochta’s; Finn Harps v Derry City; Maynooth University Town v Cobh Ramblers; Bohemians v Shamrock Rovers; Cork City v St Patrick’s Athletic; UCD v Longford Town; Killester Donnycarney v Wexford FC.