| 1. Round | 16/02/2024 | Derry City | - | Drogheda United | 2:1 | ||||
| 2. Round | 23/02/2024 | Drogheda United | - | Waterford FC | 1:4 | ||||
| 6. Round | 16/03/2024 | Sligo Rovers | - | Drogheda United | 3:1 | ||||
| 10. Round | 12/04/2024 | Drogheda United | - | Derry City | 2:2 |  |
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| 11. Round | 19/04/2024 | Bohemian FC | - | Drogheda United | 1:0 | ||||
| 12. Round | 26/04/2024 | Drogheda United | - | Sligo Rovers | 3:1 |  |
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| 3. Round | 29/04/2024 | Shamrock Rovers | - | Drogheda United | 4:0 | ||||
| 14. Round | 06/05/2024 | Drogheda United | - | Dundalk FC | 2:1 | ||||
| 28. Round | 23/08/2024 | Drogheda United | - | Sligo Rovers | 7:0 | ||||
| 29. Round | 01/09/2024 | St Patrick's Athletic | - | Drogheda United | 4:1 | ||||
| 33. Round | 11/10/2024 | Waterford FC | - | Drogheda United | 0:0 | ||||
| 35. Round | 25/10/2024 | Shelbourne FC | - | Drogheda United | 2:1 |
Ireland