3. Round | 17/08/2019 | Cliftonville FC | - | Crusaders FC | 0:2 | ||||
6. Round | 07/09/2019 | Institute FC Drumahoe | - | Crusaders FC | 0:6 | ||||
7. Round | 14/09/2019 | Crusaders FC | - | Glenavon FC | 3:2 | ||||
8. Round | 21/09/2019 | Coleraine FC | - | Crusaders FC | 4:2 | ||||
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 | ||||
15. Round | 11/11/2019 | Larne FC | - | Crusaders FC | 0:0 | ||||
16. Round | 15/11/2019 | Carrick Rangers | - | Crusaders FC | 1:3 | ||||
29. Round | 03/03/2020 | Crusaders FC | - | Cliftonville FC | 0:0 | ||||
31. Round | 07/03/2020 | Crusaders FC | - | Institute FC Drumahoe | 2:1 |