4. Round | 22/10/2019 | Linfield FC | - | Warrenpoint Town | 7:0 | ||||
13. Round | 26/10/2019 | Carrick Rangers | - | Warrenpoint Town | 1:0 | ||||
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 | ||||
20. Round | 14/12/2019 | Warrenpoint Town | - | Linfield 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 |