| 3. Round | 17/08/2019 | Glenavon FC | - | Warrenpoint Town | 2:0 |  |
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| 5. Round | 31/08/2019 | Warrenpoint Town | - | Cliftonville FC | 1:5 | |
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| 7. Round | 14/09/2019 | Warrenpoint Town | - | Carrick Rangers | 0:3 | ||||
| 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 | ||||
| 15. Round | 09/11/2019 | Cliftonville FC | - | Warrenpoint Town | 4:0 | ||||
| 22. Round | 26/12/2019 | Institute FC Drumahoe | - | Warrenpoint Town | 0:1 | ||||
| 23. Round | 28/12/2019 | Glenavon FC | - | Warrenpoint Town | 1:1 | ||||
| 24. Round | 01/01/2020 | Warrenpoint Town | - | Crusaders FC | 0:4 | ||||
| 29. Round | 14/02/2020 | Warrenpoint Town | - | Institute FC Drumahoe | 2:2 |
Ireland