| 1. Round | 04/08/2018 | Glentoran FC | - | Cliftonville FC | 1:2 | ||||
| 2. Round | 11/08/2018 | Cliftonville FC | - | Coleraine FC | 1:2 | ||||
| 3. Round | 18/08/2018 | Dungannon Swifts | - | Cliftonville FC | 1:1 | ||||
| 5. Round | 01/09/2018 | Newry City FC | - | Cliftonville FC | 1:0 | ||||
| 6. Round | 07/09/2018 | Cliftonville FC | - | Institute FC Drumahoe | 3:0 | ||||
| 7. Round | 15/09/2018 | Warrenpoint Town | - | Cliftonville FC | 2:1 | ||||
| 12. Round | 20/10/2018 | Cliftonville FC | - | Warrenpoint Town | 3:1 | ||||
| 13. Round | 27/10/2018 | Coleraine FC | - | Cliftonville FC | 1:2 | ||||
| 14. Round | 03/11/2018 | Cliftonville FC | - | Glentoran FC | 1:0 | ||||
| 18. Round | 01/12/2018 | Cliftonville FC | - | Dungannon Swifts | 5:1 | ||||
| 19. Round | 08/12/2018 | Cliftonville FC | - | Glenavon FC | 4:2 | ||||
| 20. Round | 15/12/2018 | Ards FC | - | Cliftonville FC | 1:3 | ||||
| 23. Round | 29/12/2018 | Cliftonville FC | - | Linfield FC | 0:2 | ||||
| 26. Round | 19/01/2019 | Dungannon Swifts | - | Cliftonville FC | 3:1 |
Northern Ireland