| 16. Round | 23/01/2021 | Coleraine FC | - | Dungannon Swifts | 2:0 |  |
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| 19. Round | 02/02/2021 | Ballymena United | - | Dungannon Swifts | 0:1 | |
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| 13. Round | 06/02/2021 | Dungannon Swifts | - | Carrick Rangers | 0:2 | ||||
| 21. Round | 13/02/2021 | Larne FC | - | Dungannon Swifts | 3:0 | ||||
| 12. Round | 16/02/2021 | Warrenpoint Town | - | Dungannon Swifts | 1:1 | ||||
| 22. Round | 27/02/2021 | Dungannon Swifts | - | Glentoran FC | 0:1 | ||||
| 23. Round | 02/03/2021 | Warrenpoint Town | - | Dungannon Swifts | 4:1 | ||||
| 31. Round | 13/03/2021 | Dungannon Swifts | - | Larne FC | 0:2 | |
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| 25. Round | 20/03/2021 | Dungannon Swifts | - | Portadown FC | 0:1 | ||||
| 20. Round | 23/03/2021 | Dungannon Swifts | - | Crusaders FC | 2:1 | ||||
| 26. Round | 27/03/2021 | Ballymena United | - | Dungannon Swifts | 5:1 | |
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| 27. Round | 30/03/2021 | Dungannon Swifts | - | Glenavon FC | 0:4 | |
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| 29. Round | 06/04/2021 | Cliftonville FC | - | Dungannon Swifts | 3:0 | ||||
| 30. Round | 10/04/2021 | Glentoran FC | - | Dungannon Swifts | 2:0 | ||||
| 15. Round | 13/04/2021 | Portadown FC | - | Dungannon Swifts | 1:0 | ||||
| 33. Round | 24/04/2021 | Dungannon Swifts | - | Crusaders FC | 0:2 |
Northern Ireland