| 9. Round | 03/05/2021 | Longford Town | - | Dundalk FC | 2:2 | ||||
| 10. Round | 07/05/2021 | Dundalk FC | - | Sligo Rovers | 0:1 | ||||
| 12. Round | 21/05/2021 | Dundalk FC | - | Shamrock Rovers | 2:1 |  |
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| 13. Round | 24/05/2021 | Bohemian FC | - | Dundalk FC | 5:1 | ||||
| 14. Round | 28/05/2021 | St Patrick's Athletic | - | Dundalk FC | 0:2 | ||||
| 15. Round | 11/06/2021 | Dundalk FC | - | Waterford FC | 1:3 | ||||
| 16. Round | 18/06/2021 | Dundalk FC | - | Longford Town | 1:1 | ||||
| 17. Round | 21/06/2021 | Drogheda United | - | Dundalk FC | 0:1 | ||||
| 18. Round | 25/06/2021 | Dundalk FC | - | Derry City | 2:1 | |
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| 19. Round | 02/07/2021 | Shamrock Rovers | - | Dundalk FC | 3:1 | ||||
| 21. Round | 17/07/2021 | Dundalk FC | - | Finn Harps | 1:0 | ||||
| 24. Round | 15/08/2021 | Derry City | - | Dundalk FC | 1:0 | ||||
| 26. Round | 03/09/2021 | Waterford FC | - | Dundalk FC | 1:1 | ||||
| 31. Round | 15/10/2021 | Bohemian FC | - | Dundalk FC | 1:1 | ||||
| 32. Round | 25/10/2021 | St Patrick's Athletic | - | Dundalk FC | 1:0 | ||||
| 33. Round | 29/10/2021 | Dundalk FC | - | Waterford FC | 1:0 | |
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| 35. Round | 04/11/2021 | Drogheda United | - | Dundalk FC | 0:1 | ||||
| 34. Round | 07/11/2021 | Dundalk FC | - | Longford Town | 2:0 | ||||
| 36. Round | 19/11/2021 | Dundalk FC | - | Derry City | 1:2 |
Ireland