| 2. Round | 10/08/2018 | Newry City FC | - | Dungannon Swifts | 2:1 | ||||
| 6. Round | 07/09/2018 | Glentoran FC | - | Newry City FC | 4:1 | ||||
| 7. Round | 15/09/2018 | Crusaders FC | - | Newry City FC | 1:0 | ||||
| 8. Round | 21/09/2018 | Newry City FC | - | Warrenpoint Town | 1:1 | ||||
| 14. Round | 02/11/2018 | Newry City FC | - | Crusaders FC | 0:3 | ||||
| 15. Round | 12/11/2018 | Cliftonville FC | - | Newry City FC | 3:1 | ||||
| 16. Round | 17/11/2018 | Newry City FC | - | Ards FC | 2:0 | ||||
| 17. Round | 23/11/2018 | Newry City FC | - | Ballymena United | 1:2 | ||||
| 26. Round | 19/01/2019 | Glentoran FC | - | Newry City FC | 2:1 | ||||
| 21. Round | 05/02/2019 | Newry City FC | - | Glentoran FC | 1:1 | ||||
| 28. Round | 09/02/2019 | Cliftonville FC | - | Newry City FC | 1:0 | ||||
| 32. Round | 15/03/2019 | Newry City FC | - | Coleraine FC | 1:4 | ||||
| 33. Round | 23/03/2019 | Newry City FC | - | Glenavon FC | 0:1 |
Northern Ireland