| 1. Round | 16/02/2024 | Derry City | - | Drogheda United | 2:1 | ||||
| 2. Round | 23/02/2024 | Drogheda United | - | Waterford FC | 1:4 |  |
|||
| 4. Round | 04/03/2024 | Drogheda United | - | Bohemian FC | 2:1 | ||||
| 5. Round | 08/03/2024 | Galway United | - | Drogheda United | 0:0 |  |
|||
| 6. Round | 16/03/2024 | Sligo Rovers | - | Drogheda United | 3:1 | ||||
| 7. Round | 29/03/2024 | Drogheda United | - | St Patrick's Athletic | 0:0 | ||||
| 8. Round | 01/04/2024 | Dundalk FC | - | Drogheda United | 0:0 | ||||
| 10. Round | 12/04/2024 | Drogheda United | - | Derry City | 2:2 | ||||
| 3. Round | 29/04/2024 | Shamrock Rovers | - | Drogheda United | 4:0 | ||||
| 13. Round | 03/05/2024 | St Patrick's Athletic | - | Drogheda United | 1:0 | ||||
| 15. Round | 10/05/2024 | Shelbourne FC | - | Drogheda United | 1:1 | ||||
| 16. Round | 17/05/2024 | Drogheda United | - | Galway United | 2:3 | |
|||
| 17. Round | 23/05/2024 | Waterford FC | - | Drogheda United | 4:2 | |
|||
| 18. Round | 31/05/2024 | Drogheda United | - | Shamrock Rovers | 0:2 | ||||
| 19. Round | 03/06/2024 | Sligo Rovers | - | Drogheda United | 2:1 | ||||
| 20. Round | 07/06/2024 | Drogheda United | - | St Patrick's Athletic | 0:0 | ||||
| 21. Round | 13/06/2024 | Galway United | - | Drogheda United | 3:0 |
Ireland
Nigeria