| 6. Ronde | 31.07.2020 | Derry City | - | Sligo Rovers | 0:2 | ||||
| 3. Ronde | 03.08.2020 | St Patrick's Athletic | - | Derry City | 0:2 | ||||
| 7. Ronde | 09.08.2020 | Derry City | - | Shamrock Rovers | 1:2 |  |
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| 8. Ronde | 15.08.2020 | Shelbourne FC | - | Derry City | 1:1 | ||||
| 9. Ronde | 21.08.2020 | Derry City | - | Cork City | 3:1 | |
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| 10. Ronde | 19.10.2020 | Derry City | - | Dundalk FC | 1:2 | ||||
| 17. Ronde | 23.10.2020 | Derry City | - | Shelbourne FC | 2:0 |  |
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| 16. Ronde | 07.11.2020 | Shamrock Rovers | - | Derry City | 2:0 | ||||
| 18. Ronde | 09.11.2020 | Cork City | - | Derry City | 1:1 |
Schotland