4. Round | 24/08/2019 | Ballymena United | - | Glentoran FC | 1:2 | ||||
5. Round | 02/09/2019 | Glentoran FC | - | Institute FC Drumahoe | 4:0 | ||||
6. Round | 07/09/2019 | Glentoran FC | - | Larne FC | 2:1 | ||||
9. Round | 28/09/2019 | Crusaders FC | - | Glentoran FC | 5:2 | ||||
10. Round | 04/10/2019 | Glentoran FC | - | Cliftonville FC | 0:1 | ||||
11. Round | 12/10/2019 | Glentoran FC | - | Carrick Rangers | 3:1 | ||||
13. Round | 25/10/2019 | Glentoran FC | - | Ballymena United | 3:1 | ||||
17. Round | 23/11/2019 | Glentoran FC | - | Dungannon Swifts | 6:1 | ||||
24. Round | 01/01/2020 | Dungannon Swifts | - | Glentoran FC | 0:2 | ||||
25. Round | 11/01/2020 | Glentoran FC | - | Warrenpoint Town | 2:1 | ||||
16. Round | 28/01/2020 | Glentoran FC | - | Glenavon FC | 4:0 | ||||
29. Round | 14/02/2020 | Glentoran FC | - | Carrick Rangers | 0:0 |