| 25. Round | 23/07/2022 | Shamrock Rovers | - | Drogheda United | 1:1 | ||||
| 19. Round | 01/08/2022 | Drogheda United | - | UC Dublin | 1:1 | ||||
| 27. Round | 12/08/2022 | Drogheda United | - | Shelbourne FC | 3:1 | ||||
| 29. Round | 03/09/2022 | Sligo Rovers | - | Drogheda United | 2:0 |  |
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| 31. Round | 30/09/2022 | Dundalk FC | - | Drogheda United | 2:0 | ||||
| 32. Round | 07/10/2022 | Bohemian FC | - | Drogheda United | 0:1 | ||||
| 33. Round | 16/10/2022 | Drogheda United | - | Shamrock Rovers | 1:1 | ||||
| 34. Round | 21/10/2022 | UC Dublin | - | Drogheda United | 2:1 | ||||
| 36. Round | 06/11/2022 | Drogheda United | - | Finn Harps | 2:0 |
Ireland