Dundalk defeated Derry City in the final in a penalty shoot-out, following a 2-2 draw.
[1] The competition structure was altered for 2019 with all Premier Division entering at the second round stage.
The game between Cobh Ramblers and Limerick was postponed until 18 March 2019 due to inclement weather on the original date [3] All ten League of Ireland Premier Division clubs entered at this stage of the competition.
The draw for the second round was made on 12 March 2019 with fixtures taking place on 1/2 April 2019.
[4] The draw for the quarter-final was made on 8 April 2019 with fixtures taking place on Monday, 27 May 2019.