| 1. Round | 14/02/2020 | Cork City | - | Shelbourne FC | 0:1 | ||||
| 2. Round | 21/02/2020 | Shelbourne FC | - | Dundalk FC | 1:2 | ||||
| 4. Round | 28/02/2020 | Shelbourne FC | - | St Patrick's Athletic | 1:0 | ||||
| 5. Round | 06/03/2020 | Bohemian FC | - | Shelbourne FC | 2:0 | ||||
| 3. Round | 04/08/2020 | Finn Harps | - | Shelbourne FC | 0:1 | ||||
| 7. Round | 08/08/2020 | Sligo Rovers | - | Shelbourne FC | 2:1 | ||||
| 8. Round | 15/08/2020 | Shelbourne FC | - | Derry City | 1:1 | ||||
| 16. Round | 18/10/2020 | Shelbourne FC | - | Sligo Rovers | 1:0 | ||||
| 17. Round | 23/10/2020 | Derry City | - | Shelbourne FC | 2:0 |
Ireland