EA Sports Cup holders St Patrick's Athletic face a difficult away trip to Cork City after the draw for the quarter-finals was made on Wednesday evening at FAI HQ in Abbottstown.
The Saints overcame City at the same stage two years ago as penalties were required to separate te sides following a 1-1 draw at Turner's Cross.
The Saints went on to win the first of their back-to-back league cup crowns that season as they beat Shamrock Rovers in the semi-finals and Galway United in the final, both after penalty shoot-outs.
To make it three-in-a-row, they'll have to overcome the runaway leaders of the SSE Airtricity League Premier Division, the same opposition they face in the league at Richmond Park this Friday.
League champions Dundalk play host to First Division leaders Waterford, the first time a Waterford side has reached this stage since 2010, when they were eliminated by the Lilywhites.
Last year's defeated sem-finalists Shamrock Rovers will also host First Division opposition in Longford Town, while 2015's beaten finalists Galway travel to Sligo Rovers.
All ties are expected to be played in the week beginning May 1st, with full dates and times to be confirmed. All games will be completed on the night without replays.
Full EA Sports Cup quarter-final draw:
Dundalk v Waterford
Sligo Rovers v Galway United
Shamrock Rovers v Longford Town
Cork City v St. Patrick's Athletic