| Preliminary Round | 1st Qualifying Round | 2nd Qualifying Round | 3rd Qualifying Round | Playoffs | Group Stage |
| 16th Finals | 8th Finals | Quarterfinals | Semifinals | Final |
Round:
Played
1st Round
06/27/2019 - Thursday
13:30
Barry Town United
0
x
0
Cliftonville
2nd Round
07/04/2019 - Thursday
14:45
Cliftonville
4
x
0
Barry Town United