2. Round | 22/02/2019 | Shamrock Rovers | - | Derry City | 2:0 | ||||
3. Round | 25/02/2019 | Derry City | - | Waterford FC | 3:2 | ||||
4. Round | 01/03/2019 | Cork City | - | Derry City | 0:0 | ||||
26. Round | 19/07/2019 | Derry City | - | Sligo Rovers | 3:0 | ||||
27. Round | 26/07/2019 | Finn Harps | - | Derry City | 1:0 | ||||
21. Round | 29/07/2019 | Derry City | - | Waterford FC | 2:0 | ||||
28. Round | 02/08/2019 | UC Dublin | - | Derry City | 1:3 | ||||
29. Round | 16/08/2019 | Derry City | - | Shamrock Rovers | 0:2 | ||||
30. Round | 30/08/2019 | Waterford FC | - | Derry City | 1:1 | ||||
32. Round | 20/09/2019 | Derry City | - | Bohemian FC | 0:0 | ||||
31. Round | 27/09/2019 | Derry City | - | Cork City | 4:0 | ||||
33. Round | 04/10/2019 | Dundalk FC | - | Derry City | 1:0 | ||||
35. Round | 19/10/2019 | Sligo Rovers | - | Derry City | 1:2 | ||||
34. Round | 22/10/2019 | Derry City | - | St Patrick's Athletic | 1:3 | ||||
36. Round | 25/10/2019 | Derry City | - | Finn Harps | 4:0 |