11. Round | 12/10/2019 | Dungannon Swifts | - | Linfield FC | 1:4 | ||||
12. Round | 19/10/2019 | Carrick Rangers | - | Dungannon Swifts | 1:0 | ||||
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 | ||||
18. Round | 30/11/2019 | Dungannon Swifts | - | Crusaders FC | 1:6 | ||||
19. Round | 07/12/2019 | Dungannon Swifts | - | Warrenpoint Town | 3:1 | ||||
20. Round | 14/12/2019 | Ballymena United | - | Dungannon Swifts | 3:2 | ||||
21. Round | 21/12/2019 | Dungannon Swifts | - | Institute FC Drumahoe | 2:2 | ||||
22. Round | 26/12/2019 | Glenavon FC | - | Dungannon Swifts | 5:0 | ||||
24. Round | 01/01/2020 | Dungannon Swifts | - | Glentoran FC | 0:2 |