21. Round | 29/07/2019 | Derry City | - | Waterford FC | 2:0 | ||||
28. Round | 02/08/2019 | UC Dublin | - | Derry City | 1:3 | ||||
30. Round | 30/08/2019 | Waterford FC | - | Derry City | 1:1 | ||||
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 |