1. Round | 04/08/2018 | Glentoran FC | - | Cliftonville FC | 1:2 | ||||
2. Round | 11/08/2018 | Cliftonville FC | - | Coleraine FC | 1:2 | ||||
5. Round | 01/09/2018 | Newry City FC | - | Cliftonville FC | 1:0 | ||||
6. Round | 07/09/2018 | Cliftonville FC | - | Institute FC Drumahoe | 3:0 | ||||
7. Round | 15/09/2018 | Warrenpoint Town | - | Cliftonville FC | 2:1 | ||||
18. Round | 01/12/2018 | Cliftonville FC | - | Dungannon Swifts | 5:1 | ||||
19. Round | 08/12/2018 | Cliftonville FC | - | Glenavon FC | 4:2 | ||||
20. Round | 15/12/2018 | Ards FC | - | Cliftonville FC | 1:3 | ||||
22. Round | 26/12/2018 | Cliftonville FC | - | Crusaders FC | 1:5 | ||||
27. Round | 26/01/2019 | Cliftonville FC | - | Glenavon FC | 1:1 | ||||
33. Round | 30/03/2019 | Cliftonville FC | - | Glentoran FC | 2:1 |