The defending champions were Premier Division side Dundalk, after they defeated Cork City 2–1 in the previous final.
Former Republic of Ireland international Keith Fahey and FAI Vice President Noel Fitzroy performed the draw, with representatives from the clubs in attendance.
Four teams received byes into the first round of the competition: Cobh Wanderers, Crumlin United, Letterkenny Rovers and Killester Donnycarney.
The draw for the first round took place on 8 July 2019 at the Aviva Stadium in Dublin, and was hosted by Con Murphy.
The draw for the semi-finals took place on 12 September 2019 and was broadcast live on Morning Ireland on RTÉ Radio 1.