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 | ||||
7. Round | 14/09/2019 | Dungannon Swifts | - | Cliftonville FC | 0:4 | ||||
8. Round | 21/09/2019 | Larne FC | - | Dungannon Swifts | 0:0 | ||||
12. Round | 19/10/2019 | Carrick Rangers | - | Dungannon Swifts | 1:0 | ||||
20. Round | 14/12/2019 | Ballymena United | - | Dungannon Swifts | 3:2 |