| 16. Round | 16/11/2019 | Warrenpoint Town | - | Coleraine FC | 3:1 |  |
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| 17. Round | 23/11/2019 | Warrenpoint Town | - | Crusaders FC | 0:1 | ||||
| 18. Round | 30/11/2019 | Warrenpoint Town | - | Ballymena United | 2:1 | |
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| 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 | ||||
| 23. Round | 28/12/2019 | Glenavon FC | - | Warrenpoint Town | 1:1 | |
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| 24. Round | 01/01/2020 | Warrenpoint Town | - | Crusaders FC | 0:4 | ||||
| 25. Round | 11/01/2020 | Glentoran FC | - | Warrenpoint Town | 2:1 |  |
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| 26. Round | 18/01/2020 | Warrenpoint Town | - | Coleraine FC | 0:4 | ||||
| 27. Round | 25/01/2020 | Carrick Rangers | - | Warrenpoint Town | 1:2 |
Ireland