1. Round | 10/08/2019 | Crusaders FC | - | Carrick Rangers | 3:0 | ||||
4. Round | 24/08/2019 | Crusaders FC | - | Larne FC | 2:2 | ||||
6. Round | 07/09/2019 | Institute FC Drumahoe | - | Crusaders FC | 0:6 | ||||
8. Round | 21/09/2019 | Coleraine FC | - | Crusaders FC | 4:2 | ||||
12. Round | 19/10/2019 | Crusaders FC | - | Coleraine FC | 0:2 |