1. Round | 10/08/2019 | Crusaders FC | - | Carrick Rangers | 3:0 | ||||
2. Round | 13/08/2019 | Crusaders FC | - | Warrenpoint Town | 4:0 | ||||
5. Round | 31/08/2019 | Crusaders FC | - | Dungannon Swifts | 3:0 | ||||
9. Round | 28/09/2019 | Crusaders FC | - | Glentoran FC | 5:2 | ||||
10. Round | 04/10/2019 | Crusaders FC | - | Linfield FC | 1:0 | ||||
11. Round | 12/10/2019 | Ballymena United | - | Crusaders FC | 1:1 | ||||
13. Round | 26/10/2019 | Glenavon FC | - | Crusaders FC | 2:2 | ||||
14. Round | 02/11/2019 | Crusaders FC | - | Institute FC Drumahoe | 1:1 | ||||
21. Round | 21/12/2019 | Linfield FC | - | Crusaders FC | 1:1 | ||||
23. Round | 28/12/2019 | Crusaders FC | - | Dungannon Swifts | 5:0 | ||||
24. Round | 01/01/2020 | Warrenpoint Town | - | Crusaders FC | 0:4 | ||||
25. Round | 10/01/2020 | Coleraine FC | - | Crusaders FC | 0:1 | ||||
26. Round | 18/01/2020 | Crusaders FC | - | Larne FC | 3:0 | ||||
27. Round | 25/01/2020 | Crusaders FC | - | Ballymena United | 2:0 | ||||
28. Round | 08/02/2020 | Glenavon FC | - | Crusaders FC | 2:1 | ||||
30. Round | 21/02/2020 | Linfield FC | - | Crusaders FC | 4:0 | ||||
31. Round | 07/03/2020 | Crusaders FC | - | Institute FC Drumahoe | 2:1 |