| 6. Round | 20/04/2021 | Drogheda United | - | Shamrock Rovers | 0:1 | ||||
| 7. Round | 24/04/2021 | Dundalk FC | - | Drogheda United | 2:1 | ||||
| 8. Round | 30/04/2021 | Drogheda United | - | Sligo Rovers | 1:1 | ||||
| 9. Round | 03/05/2021 | Drogheda United | - | Bohemian FC | 1:1 | ||||
| 13. Round | 24/05/2021 | Drogheda United | - | Longford Town | 4:1 |
Ireland