| 8. Round | 15/09/2018 | Carlisle United | - | Tranmere Rovers | 0:2 | ||||
| 10. Round | 29/09/2018 | Carlisle United | - | Stevenage FC | 0:1 | ||||
| 11. Round | 02/10/2018 | Carlisle United | - | Grimsby Town | 0:1 | ||||
| 13. Round | 13/10/2018 | Carlisle United | - | Morecambe FC | 0:2 | ||||
| 14. Round | 20/10/2018 | Macclesfield Town | - | Carlisle United | 2:1 | ||||
| 16. Round | 27/10/2018 | Carlisle United | - | Yeovil Town | 0:1 | ||||
| 18. Round | 17/11/2018 | Swindon Town | - | Carlisle United | 0:4 | ||||
| 20. Round | 27/11/2018 | Notts County | - | Carlisle United | 1:1 | ||||
| 24. Round | 26/12/2018 | Carlisle United | - | Oldham Athletic | 6:0 | ||||
| 27. Round | 05/01/2019 | Carlisle United | - | Mansfield Town | 3:2 | ||||
| 28. Round | 12/01/2019 | Northampton Town | - | Carlisle United | 3:0 | ||||
| 29. Round | 19/01/2019 | Carlisle United | - | Cheltenham Town | 2:0 | ||||
| 30. Round | 26/01/2019 | Port Vale FC | - | Carlisle United | 0:1 | ||||
| 33. Round | 16/02/2019 | Carlisle United | - | Milton Keynes Dons | 2:3 | ||||
| 34. Round | 23/02/2019 | Colchester United | - | Carlisle United | 1:1 | ||||
| 35. Round | 02/03/2019 | Newport County | - | Carlisle United | 2:0 |
England