Primera ronda
23.07.2021 20:45 Wexford FC Wexford FC - Cabinteely FC Cabinteely FC 3:0
23.07.2021 20:45 UC Dublin UC Dublin - Shelbourne FC Shelbourne FC 2:0
23.07.2021 20:45 Athlone Town Athlone Town - Waterford FC Waterford FC 2:4 (0:1, 3:3, 4:4) pn.
23.07.2021 20:45 St Patrick's Athletic St Patrick's Athletic - Bray Wanderers Bray Wanderers 6:0
23.07.2021 21:00 St. Kevin's Boys St. Kevin's Boys - Kilnamanagh AFC Kilnamanagh AFC 1:4
23.07.2021 21:00 Shamrock Rovers Shamrock Rovers - Galway United Galway United 2:0
23.07.2021 21:00 Maynooth University Town Maynooth University Town - Malahide United Malahide United 4:0
24.07.2021 16:00 Drogheda United Drogheda United - Derry City Derry City 2:4 (1:0, 1:1, 1:1) pn.
24.07.2021 17:00 Fairview Rangers Fairview Rangers - Finn Harps Finn Harps 0:3 (0:0) pró.
24.07.2021 20:30 Longford Town Longford Town - Bangor GG FC Bangor GG FC 5:0 (1:0)
25.07.2021 12:00 Killester Donnycarney FC Killester Donnycarney FC - Usher Celtic Usher Celtic 1:0 (0:0)
25.07.2021 15:00 Liffey Wanderers Liffey Wanderers - Cobh Ramblers Cobh Ramblers 0:2 pró.
25.07.2021 15:00 Crumlin United Crumlin United - St. Mochta's St. Mochta's 1:2
25.07.2021 15:00 Treaty United Treaty United - Dundalk FC Dundalk FC 0:1 pró.
25.07.2021 16:00 College Corinthians College Corinthians - Bohemian FC Bohemian FC 0:5
25.07.2021 18:00 Sligo Rovers Sligo Rovers - Cork City Cork City 2:3 (1:1)
Octavos de final
28.08.2021 Waterford FC Waterford FC - Kilnamanagh AFC Kilnamanagh AFC -:-
28.08.2021 Dundalk FC Dundalk FC - St. Mochta's St. Mochta's -:-
28.08.2021 Finn Harps Finn Harps - Derry City Derry City -:-
28.08.2021 Maynooth University Town Maynooth University Town - Cobh Ramblers Cobh Ramblers -:-
28.08.2021 Bohemian FC Bohemian FC - Cobh Ramblers Cobh Ramblers -:-
28.08.2021 Bohemian FC Bohemian FC - Shamrock Rovers Shamrock Rovers -:-
28.08.2021 Cork City Cork City - St Patrick's Athletic St Patrick's Athletic -:-
28.08.2021 UC Dublin UC Dublin - Longford Town Longford Town -:-
28.08.2021 Killester Donnycarney FC Killester Donnycarney FC - Wexford FC Wexford FC -:-