7. Round | 31/03/2023 | Cork City | - | Drogheda United | 1:1 | ||||
8. Round | 07/04/2023 | Derry City | - | Drogheda United | 0:1 | ||||
9. Round | 10/04/2023 | Drogheda United | - | St Patrick's Athletic | 1:3 | ||||
10. Round | 15/04/2023 | Sligo Rovers | - | Drogheda United | 1:1 | ||||
11. Round | 21/04/2023 | Drogheda United | - | Bohemian FC | 0:2 | ||||
34. Round | 22/10/2023 | Shamrock Rovers | - | Drogheda United | 5:0 | ||||
36. Round | 03/11/2023 | Drogheda United | - | Shelbourne FC | 2:4 |