1. Round | 10/08/2019 | Coleraine FC | - | Cliftonville FC | 1:1 | ||||
2. Round | 13/08/2019 | Cliftonville FC | - | Glenavon FC | 3:1 | ||||
3. Round | 17/08/2019 | Cliftonville FC | - | Crusaders FC | 0:2 | ||||
4. Round | 24/08/2019 | Carrick Rangers | - | Cliftonville FC | 0:1 | ||||
5. Round | 31/08/2019 | Warrenpoint Town | - | Cliftonville FC | 1:5 | ||||
6. Round | 07/09/2019 | Cliftonville FC | - | Linfield FC | 0:1 | ||||
7. Round | 14/09/2019 | Dungannon Swifts | - | Cliftonville FC | 0:4 | ||||
8. Round | 21/09/2019 | Cliftonville FC | - | Institute FC Drumahoe | 1:0 | ||||
24. Round | 01/01/2020 | Cliftonville FC | - | Glenavon FC | 1:0 | ||||
27. Round | 27/01/2020 | Coleraine FC | - | Cliftonville FC | 1:0 | ||||
20. Round | 04/02/2020 | Cliftonville FC | - | Carrick Rangers | 3:1 | ||||
28. Round | 08/02/2020 | Cliftonville FC | - | Dungannon Swifts | 1:1 |