| 2. Round | 11/08/2023 | Ballymena United | - | Crusaders FC | 1:2 | ||||
| 1. Round | 22/08/2023 | Crusaders FC | - | Carrick Rangers | 9:0 |  |
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| 5. Round | 26/08/2023 | Newry City FC | - | Crusaders FC | 0:4 | ||||
| 8. Round | 18/09/2023 | Crusaders FC | - | Cliftonville FC | 0:3 | ||||
| 9. Round | 23/09/2023 | Crusaders FC | - | Glenavon FC | 2:0 | ||||
| 7. Round | 26/09/2023 | Linfield FC | - | Crusaders FC | 2:0 | ||||
| 10. Round | 30/09/2023 | Coleraine FC | - | Crusaders FC | 0:4 | ||||
| 12. Round | 13/10/2023 | Crusaders FC | - | Ballymena United | 1:0 | ||||
| 13. Round | 21/10/2023 | Dungannon Swifts | - | Crusaders FC | 1:4 | |
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| 15. Round | 04/11/2023 | Crusaders FC | - | Coleraine FC | 0:2 | ||||
| 18. Round | 25/11/2023 | Cliftonville FC | - | Crusaders FC | 3:0 | ||||
| 21. Round | 15/12/2023 | Crusaders FC | - | Larne FC | 0:3 | ||||
| 23. Round | 26/12/2023 | Cliftonville FC | - | Crusaders FC | 2:1 | ||||
| 24. Round | 30/12/2023 | Crusaders FC | - | Carrick Rangers | 2:0 | ||||
| 17. Round | 02/01/2024 | Crusaders FC | - | Linfield FC | 0:1 |
Northern Ireland