1. Round | 10/08/2019 | Linfield FC | - | Institute FC Drumahoe | 3:1 | ||||
2. Round | 13/08/2019 | Institute FC Drumahoe | - | Dungannon Swifts | 2:3 | ||||
3. Round | 17/08/2019 | Institute FC Drumahoe | - | Carrick Rangers | 0:2 | ||||
7. Round | 14/09/2019 | Institute FC Drumahoe | - | Larne FC | 1:4 | ||||
8. Round | 21/09/2019 | Cliftonville FC | - | Institute FC Drumahoe | 1:0 | ||||
9. Round | 28/09/2019 | Warrenpoint Town | - | Institute FC Drumahoe | 1:3 | ||||
10. Round | 05/10/2019 | Institute FC Drumahoe | - | Ballymena United | 1:1 | ||||
13. Round | 26/10/2019 | Larne FC | - | Institute FC Drumahoe | 1:1 | ||||
14. Round | 02/11/2019 | Crusaders FC | - | Institute FC Drumahoe | 1:1 | ||||
15. Round | 09/11/2019 | Institute FC Drumahoe | - | Glentoran FC | 1:1 | ||||
16. Round | 16/11/2019 | Institute FC Drumahoe | - | Linfield FC | 0:3 | ||||
17. Round | 23/11/2019 | Ballymena United | - | Institute FC Drumahoe | 1:1 | ||||
11. Round | 26/11/2019 | Glenavon FC | - | Institute FC Drumahoe | 3:1 | ||||
21. Round | 21/12/2019 | Dungannon Swifts | - | Institute FC Drumahoe | 2:2 |