| 5. Round | 10/11/2020 | Dungannon Swifts | - | Cliftonville FC | 2:1 |  |
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| 7. Round | 21/11/2020 | Crusaders FC | - | Dungannon Swifts | 3:1 | |
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| 14. Round | 02/01/2021 | Dungannon Swifts | - | Cliftonville FC | 1:2 | ||||
| 16. Round | 23/01/2021 | Coleraine FC | - | Dungannon Swifts | 2:0 | ||||
| 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 | |
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| 23. Round | 02/03/2021 | Warrenpoint Town | - | Dungannon Swifts | 4:1 | ||||
| 24. Round | 06/03/2021 | Dungannon Swifts | - | Coleraine FC | 2:3 | |
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| 31. Round | 13/03/2021 | Dungannon Swifts | - | Larne FC | 0:2 | |
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| 18. Round | 16/03/2021 | Linfield FC | - | Dungannon Swifts | 2:0 | |
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| 20. Round | 23/03/2021 | Dungannon Swifts | - | Crusaders FC | 2:1 | ||||
| 26. Round | 27/03/2021 | Ballymena United | - | Dungannon Swifts | 5:1 |
Northern Ireland