| 1. Round | 10/08/2019 | Linfield FC | - | Institute FC Drumahoe | 3:1 | ||||
| 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 |  |
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| 20. Round | 14/12/2019 | Institute FC Drumahoe | - | Glenavon FC | 1:4 |  |
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| 23. Round | 28/12/2019 | Institute FC Drumahoe | - | Carrick Rangers | 0:3 | ||||
| 24. Round | 01/01/2020 | Linfield FC | - | Institute FC Drumahoe | 3:0 |
Northern Ireland