2. Round | 13/08/2019 | Crusaders FC | - | Warrenpoint Town | 4:0 | ||||
3. Round | 17/08/2019 | Cliftonville FC | - | Crusaders FC | 0:2 | ||||
4. Round | 24/08/2019 | Crusaders FC | - | Larne FC | 2:2 | ||||
5. Round | 31/08/2019 | Crusaders FC | - | Dungannon Swifts | 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 | ||||
8. Round | 21/09/2019 | Coleraine FC | - | Crusaders FC | 4:2 | ||||
9. Round | 28/09/2019 | Crusaders FC | - | Glentoran FC | 5:2 | ||||
10. Round | 04/10/2019 | Crusaders FC | - | Linfield FC | 1:0 | ||||
12. Round | 19/10/2019 | Crusaders FC | - | Coleraine FC | 0:2 | ||||
18. Round | 30/11/2019 | Dungannon Swifts | - | Crusaders FC | 1:6 | ||||
20. Round | 14/12/2019 | Glentoran FC | - | Crusaders FC | 1:1 | ||||
21. Round | 21/12/2019 | Linfield FC | - | Crusaders FC | 1:1 | ||||
22. Round | 26/12/2019 | Crusaders FC | - | Cliftonville FC | 1:2 | ||||
29. Round | 03/03/2020 | Crusaders FC | - | Cliftonville FC | 0:0 |