| 1. Round | 17/10/2020 | Larne FC | - | Dungannon Swifts | 3:0 | ||||
| 2. Round | 24/10/2020 | Dungannon Swifts | - | Warrenpoint Town | 0:2 | ||||
| 10. Round | 12/12/2020 | Dungannon Swifts | - | Ballymena United | 1:5 | ||||
| 11. Round | 19/12/2020 | Linfield FC | - | Dungannon Swifts | 4:0 | ||||
| 14. Round | 02/01/2021 | Dungannon Swifts | - | Cliftonville FC | 1:2 | ||||
| 13. Round | 06/02/2021 | Dungannon Swifts | - | Carrick Rangers | 0:2 | ||||
| 24. Round | 06/03/2021 | Dungannon Swifts | - | Coleraine FC | 2:3 | ||||
| 18. Round | 16/03/2021 | Linfield FC | - | Dungannon Swifts | 2:0 | ||||
| 25. Round | 20/03/2021 | Dungannon Swifts | - | Portadown FC | 0:1 | ||||
| 28. Round | 03/04/2021 | Dungannon Swifts | - | Linfield FC | 0:2 | ||||
| 29. Round | 06/04/2021 | Cliftonville FC | - | Dungannon Swifts | 3:0 | ||||
| 30. Round | 10/04/2021 | Glentoran FC | - | Dungannon Swifts | 2:0 | ||||
| 32. Round | 16/04/2021 | Carrick Rangers | - | Dungannon Swifts | 1:1 |
Northern Ireland