 |
 |
| 1. Round | ||||||
|---|---|---|---|---|---|---|
| 04/10/2019 | 19:45 | Cabinteely FC | - | Longford Town | 0:0 (0:0) | |
| 11/10/2019 | 19:45 | Longford Town | - | Cabinteely FC | 1:3 (1:1, 1:1, 1:1) pso | |
| 2. Round | ||||||
| 18/10/2019 | 19:45 | Cabinteely FC | - | Drogheda United | 1:1 (1:0) | |
| 25/10/2019 | 19:45 | Drogheda United | - | Cabinteely FC | 5:1 (1:0) | |
| Final | ||||||
| 28/10/2019 | 19:45 | Drogheda United | - | Finn Harps | 1:0 (0:0) | |
| 01/11/2019 | 19:45 | Finn Harps | - | Drogheda United | 2:0 (1:0, 1:0) aet | |
