| 1. Round | 06/08/2018 | Crusaders FC | - | Ards FC | 4:2 |  |
|||
| 2. Round | 11/08/2018 | Crusaders FC | - | Ballymena United | 2:2 | ||||
| 4. Round | 25/08/2018 | Warrenpoint Town | - | Crusaders FC | 1:2 | ||||
| 5. Round | 03/09/2018 | Crusaders FC | - | Coleraine FC | 0:3 | |
|||
| 8. Round | 22/09/2018 | Glenavon FC | - | Crusaders FC | 3:2 | ||||
| 6. Round | 25/09/2018 | Dungannon Swifts | - | Crusaders FC | 3:2 | ||||
| 9. Round | 29/09/2018 | Institute FC Drumahoe | - | Crusaders FC | 1:4 | ||||
| 12. Round | 20/10/2018 | Coleraine FC | - | Crusaders FC | 1:0 | ||||
| 13. Round | 27/10/2018 | Ballymena United | - | Crusaders FC | 3:0 | ||||
| 14. Round | 02/11/2018 | Newry City FC | - | Crusaders FC | 0:3 | ||||
| 15. Round | 10/11/2018 | Ards FC | - | Crusaders FC | 0:1 | ||||
| 16. Round | 17/11/2018 | Crusaders FC | - | Glenavon FC | 3:0 | ||||
| 20. Round | 15/12/2018 | Crusaders FC | - | Dungannon Swifts | 1:0 | ||||
| 21. Round | 22/12/2018 | Crusaders FC | - | Warrenpoint Town | 3:1 | |
|||
| 22. Round | 26/12/2018 | Cliftonville FC | - | Crusaders FC | 1:5 | ||||
| 23. Round | 29/12/2018 | Glentoran FC | - | Crusaders FC | 0:1 | ||||
| 26. Round | 19/01/2019 | Crusaders FC | - | Linfield FC | 0:1 | |
|||
| 33. Round | 23/03/2019 | Ards FC | - | Crusaders FC | 2:2 |
Northern Ireland