1. Round | 04/08/2018 | Glentoran FC | - | Cliftonville FC | 1:2 | ||||
2. Round | 11/08/2018 | Cliftonville FC | - | Coleraine FC | 1:2 | ||||
3. Round | 18/08/2018 | Dungannon Swifts | - | Cliftonville FC | 1:1 | ||||
5. Round | 01/09/2018 | Newry City FC | - | Cliftonville FC | 1:0 | ||||
17. Round | 24/11/2018 | Linfield FC | - | Cliftonville FC | 4:2 | ||||
21. Round | 22/12/2018 | Institute FC Drumahoe | - | Cliftonville FC | 6:4 | ||||
22. Round | 26/12/2018 | Cliftonville FC | - | Crusaders FC | 1:5 | ||||
24. Round | 01/01/2019 | Coleraine FC | - | Cliftonville FC | 4:1 | ||||
25. Round | 12/01/2019 | Cliftonville FC | - | Ards FC | 4:1 | ||||
26. Round | 19/01/2019 | Dungannon Swifts | - | Cliftonville FC | 3:1 | ||||
30. Round | 23/02/2019 | Warrenpoint Town | - | Cliftonville FC | 0:2 | ||||
29. Round | 26/02/2019 | Ballymena United | - | Cliftonville FC | 2:1 | ||||
11. Round | 02/03/2019 | Glenavon FC | - | Cliftonville FC | 0:2 | ||||
31. Round | 09/03/2019 | Cliftonville FC | - | Institute FC Drumahoe | 1:0 | ||||
32. Round | 16/03/2019 | Crusaders FC | - | Cliftonville FC | 2:0 | ||||
33. Round | 30/03/2019 | Cliftonville FC | - | Glentoran FC | 2:1 |