| 1. Round | 10/08/2019 | Dungannon Swifts | - | Ballymena United | 2:2 |  |
|||
| 2. Round | 13/08/2019 | Institute FC Drumahoe | - | Dungannon Swifts | 2:3 | ||||
| 3. Round | 17/08/2019 | Dungannon Swifts | - | Glentoran FC | 3:1 | ||||
| 4. Round | 24/08/2019 | Dungannon Swifts | - | Glenavon FC | 2:1 | ||||
| 5. Round | 31/08/2019 | Crusaders FC | - | Dungannon Swifts | 3:0 | ||||
| 13. Round | 26/10/2019 | Cliftonville FC | - | Dungannon Swifts | 5:0 | ||||
| 14. Round | 02/11/2019 | Dungannon Swifts | - | Coleraine FC | 0:2 | ||||
| 16. Round | 16/11/2019 | Dungannon Swifts | - | Larne FC | 0:1 | ||||
| 17. Round | 23/11/2019 | Glentoran FC | - | Dungannon Swifts | 6:1 | |
|||
| 22. Round | 26/12/2019 | Glenavon FC | - | Dungannon Swifts | 5:0 | ||||
| 23. Round | 28/12/2019 | Crusaders FC | - | Dungannon Swifts | 5:0 | ||||
| 24. Round | 01/01/2020 | Dungannon Swifts | - | Glentoran FC | 0:2 |
Northern Ireland