| 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 | ||||
| 18. Round | 30/11/2019 | Warrenpoint Town | - | Ballymena United | 2:1 | ||||
| 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 | ||||
| 22. Round | 26/12/2019 | Institute FC Drumahoe | - | Warrenpoint Town | 0:1 | ||||
| 24. Round | 01/01/2020 | Warrenpoint Town | - | Crusaders FC | 0:4 | ||||
| 30. Round | 22/02/2020 | Larne FC | - | Warrenpoint Town | 1:0 |
Northern Ireland