| 1. Ronde | 15.02.2019 | Derry City | - | UC Dublin | 3:0 | ||||
| 2. Ronde | 22.02.2019 | Shamrock Rovers | - | Derry City | 2:0 |  |
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| 5. Ronde | 08.03.2019 | Bohemian FC | - | Derry City | 1:1 | ||||
| 8. Ronde | 29.03.2019 | Derry City | - | Sligo Rovers | 2:0 | ||||
| 7. Ronde | 15.04.2019 | St Patrick's Athletic | - | Derry City | 1:3 | ||||
| 12. Ronde | 22.04.2019 | Waterford FC | - | Derry City | 2:2 | ||||
| 25. Ronde | 21.05.2019 | St Patrick's Athletic | - | Derry City | 1:0 | ||||
| 18. Ronde | 24.05.2019 | Derry City | - | Finn Harps | 4:0 | ||||
| 20. Ronde | 08.06.2019 | Shamrock Rovers | - | Derry City | 2:2 | |
Schotland