5. Round | 31/08/2019 | Warrenpoint Town | - | Cliftonville FC | 1:5 | ||||
6. Round | 07/09/2019 | Ballymena United | - | Warrenpoint Town | 4:0 | ||||
10. Round | 05/10/2019 | Warrenpoint Town | - | Dungannon Swifts | 4:3 | ||||
12. Round | 19/10/2019 | Warrenpoint Town | - | Glenavon FC | 1:3 | ||||
14. Round | 02/11/2019 | Warrenpoint Town | - | Glentoran FC | 0:4 | ||||
15. Round | 09/11/2019 | Cliftonville FC | - | Warrenpoint Town | 4:0 | ||||
16. Round | 16/11/2019 | Warrenpoint Town | - | Coleraine FC | 3:1 | ||||
17. Round | 23/11/2019 | Warrenpoint Town | - | Crusaders FC | 0:1 | ||||
19. Round | 07/12/2019 | Dungannon Swifts | - | Warrenpoint Town | 3:1 | ||||
20. Round | 14/12/2019 | Warrenpoint Town | - | Linfield FC | 0:2 | ||||
21. Round | 21/12/2019 | Warrenpoint Town | - | Larne FC | 0:2 | ||||
23. Round | 28/12/2019 | Glenavon FC | - | Warrenpoint Town | 1:1 | ||||
24. Round | 01/01/2020 | Warrenpoint Town | - | Crusaders FC | 0:4 |