| 1. Round | 20/03/2021 | Longford Town | - | Derry City | 2:0 | ||||
| 4. Round | 10/04/2021 | Longford Town | - | Drogheda United | 0:4 | ||||
| 6. Round | 20/04/2021 | Longford Town | - | Finn Harps | 0:0 | ||||
| 8. Round | 30/04/2021 | St Patrick's Athletic | - | Longford Town | 3:0 |  |
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| 9. Round | 03/05/2021 | Longford Town | - | Dundalk FC | 2:2 | ||||
| 12. Round | 21/05/2021 | Sligo Rovers | - | Longford Town | 2:0 | ||||
| 14. Round | 29/05/2021 | Longford Town | - | Shamrock Rovers | 0:1 | ||||
| 18. Round | 25/06/2021 | Finn Harps | - | Longford Town | 1:1 | ||||
| 19. Round | 03/07/2021 | Longford Town | - | Sligo Rovers | 0:1 | ||||
| 20. Round | 10/07/2021 | Longford Town | - | Drogheda United | 1:1 | ||||
| 21. Round | 18/07/2021 | Bohemian FC | - | Longford Town | 1:1 | |
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| 22. Round | 31/07/2021 | Longford Town | - | Derry City | 0:2 | ||||
| 23. Round | 08/08/2021 | Shamrock Rovers | - | Longford Town | 1:0 | ||||
| 26. Round | 03/09/2021 | St Patrick's Athletic | - | Longford Town | 3:2 | ||||
| 27. Round | 11/09/2021 | Longford Town | - | Dundalk FC | 1:0 | ||||
| 28. Round | 24/09/2021 | Derry City | - | Longford Town | 3:0 | ||||
| 35. Round | 13/11/2021 | Longford Town | - | Waterford FC | 1:1 | ||||
| 36. Round | 19/11/2021 | Finn Harps | - | Longford Town | 5:0 |
Ireland