2. Round | 11/08/2018 | Crusaders FC | - | Ballymena United | 2:2 | ||||
3. Round | 18/08/2018 | Crusaders FC | - | Linfield FC | 0:2 | ||||
4. Round | 25/08/2018 | Warrenpoint Town | - | Crusaders FC | 1:2 | ||||
19. Round | 08/12/2018 | Linfield FC | - | Crusaders FC | 4:1 | ||||
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 | ||||
24. Round | 01/01/2019 | Crusaders FC | - | Ballymena United | 3:2 | ||||
26. Round | 19/01/2019 | Crusaders FC | - | Linfield FC | 0:1 | ||||
28. Round | 09/02/2019 | Dungannon Swifts | - | Crusaders FC | 1:0 | ||||
29. Round | 15/02/2019 | Crusaders FC | - | Coleraine FC | 4:2 | ||||
30. Round | 22/02/2019 | Crusaders FC | - | Glenavon FC | 1:1 | ||||
31. Round | 19/03/2019 | Warrenpoint Town | - | Crusaders FC | 1:3 | ||||
33. Round | 23/03/2019 | Ards FC | - | Crusaders FC | 2:2 |