1. Round | 10/08/2019 | Larne FC | - | Warrenpoint Town | 6:0 | ||||
2. Round | 13/08/2019 | Crusaders FC | - | Warrenpoint Town | 4:0 | ||||
3. Round | 17/08/2019 | Glenavon FC | - | Warrenpoint Town | 2:0 | ||||
10. Round | 05/10/2019 | Warrenpoint Town | - | Dungannon Swifts | 4:3 | ||||
11. Round | 12/10/2019 | Coleraine FC | - | Warrenpoint Town | 3:0 | ||||
12. Round | 19/10/2019 | Warrenpoint Town | - | Glenavon FC | 1:3 | ||||
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 | ||||
25. Round | 11/01/2020 | Glentoran FC | - | Warrenpoint Town | 2:1 |