1. Round | 10/08/2019 | Crusaders FC | - | Carrick Rangers | 3:0 | ||||
6. Round | 07/09/2019 | Institute FC Drumahoe | - | Crusaders FC | 0:6 | ||||
7. Round | 14/09/2019 | Crusaders FC | - | Glenavon FC | 3:2 | ||||
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 | ||||
16. Round | 15/11/2019 | Carrick Rangers | - | Crusaders FC | 1:3 | ||||
17. Round | 23/11/2019 | Warrenpoint Town | - | Crusaders FC | 0:1 | ||||
18. Round | 30/11/2019 | Dungannon Swifts | - | Crusaders FC | 1:6 | ||||
19. Round | 07/12/2019 | Crusaders FC | - | Ballymena United | 0:1 | ||||
20. Round | 14/12/2019 | Glentoran FC | - | Crusaders FC | 1:1 | ||||
30. Round | 21/02/2020 | Linfield FC | - | Crusaders FC | 4:0 |