12. Round | 19/10/2019 | Institute FC Drumahoe | - | Cliftonville FC | 0:3 | ||||
13. Round | 26/10/2019 | Cliftonville FC | - | Dungannon Swifts | 5:0 | ||||
15. Round | 09/11/2019 | Cliftonville FC | - | Warrenpoint Town | 4:0 | ||||
17. Round | 23/11/2019 | Larne FC | - | Cliftonville FC | 1:1 |