| 24. Round | 15/08/2021 | Drogheda United | - | Shamrock Rovers | 0:1 | ||||
| 25. Round | 20/08/2021 | Dundalk FC | - | Drogheda United | 1:2 | ||||
| 26. Round | 03/09/2021 | Drogheda United | - | Sligo Rovers | 0:0 | ||||
| 27. Round | 10/09/2021 | Drogheda United | - | Bohemian FC | 3:2 |  |
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| 28. Round | 24/09/2021 | Waterford FC | - | Drogheda United | 1:0 | ||||
| 29. Round | 01/10/2021 | Drogheda United | - | St Patrick's Athletic | 0:1 | ||||
| 31. Round | 15/10/2021 | Drogheda United | - | Longford Town | 2:0 | ||||
| 32. Round | 24/10/2021 | Drogheda United | - | Derry City | 1:0 | ||||
| 33. Round | 29/10/2021 | Sligo Rovers | - | Drogheda United | 2:0 | ||||
| 30. Round | 01/11/2021 | Finn Harps | - | Drogheda United | 0:0 | ||||
| 35. Round | 04/11/2021 | Drogheda United | - | Dundalk FC | 0:1 | ||||
| 34. Round | 07/11/2021 | Bohemian FC | - | Drogheda United | 2:1 | ||||
| 36. Round | 19/11/2021 | Shamrock Rovers | - | Drogheda United | 2:1 |
Ireland