First round
All ten teams from the League of Ireland First Division, with the exception of Shamrock Rovers II, enter the competition at this stage. One representative from the Leinster Senior League. the Munster Senior League and the Ulster Senior League enter at this point also. The draw for the first round was made on 18 February with fixtures originally set for 9 and 10 March. [2]
| 8 March 2020 | Cabinteely | 4–3 (a.e.t.) | Crumlin United | Blackrock, Dublin |
| 15:30 GMT | Kaito Akimoto  1'Eoin McPhillips 15'Dean Casey 109'Oliver White 119' | Report | Stephen Larkin 19' Craig Walsh 34' (pen.)103' | Stadium: Stradbrook Road Attendance: 150 (est.) Referee: Robert Dowling |
| 10 March 2020 | UCC | 1–1 (a.e.t.) (3–4 p) | Cobh Ramblers | Cork |
| 19:30 GMT | Owen Collins 107' | Report | Cian Leonard 105' | Stadium: The Mardyke Attendance: 200 (est.) Referee: Kevin O'Sullivan |
| Penalties | ||||
Daniel Pender  James Sheehan  Daniel Pender Gordon Walker Rian O'Sullivan | David Hurley Cian Leonard Pierce Phillips Adam Foley Charlie Lyons | |||
| 10 March 2020 | Galway United | 2–0 | Athlone Town | Galway |
| 19:45 GMT | Alberto Cabanyes 49' Wilson Waweru 65' | Report | Stadium: Eamon Deacy Park Attendance: 350 (est.) Referee: Damien McGraith |
| 10 March 2020 | Wexford | 1–2 (a.e.t.) | Bray Wanderers | Wexford |
| 19:45 GMT | Janabi Amour 55' | Report | Joe Doyle 90+3'108' | Stadium: Ferrycarrig Park Attendance: 150 (est.) Referee: Alan Patchell |
| Cancelled | Longford Town | C–C | Cockhill Celtic | Longford |
| Stadium: Bishopsgate |
| Cancelled | Drogheda United | C–C | UCD | Drogheda |
| Stadium: United Park |
