| 14. Round | 19/10/2019 | Plymouth Argyle | - | Carlisle United | 2:0 |  |
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| 15. Round | 22/10/2019 | Carlisle United | - | Northampton Town | 0:2 | ||||
| 16. Round | 26/10/2019 | Leyton Orient | - | Carlisle United | 1:1 | ||||
| 17. Round | 02/11/2019 | Carlisle United | - | Macclesfield Town | 2:1 | ||||
| 18. Round | 16/11/2019 | Port Vale FC | - | Carlisle United | 2:1 | ||||
| 19. Round | 23/11/2019 | Carlisle United | - | Cambridge United | 0:0 | ||||
| 20. Round | 07/12/2019 | Morecambe FC | - | Carlisle United | 1:1 | |
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| 21. Round | 14/12/2019 | Carlisle United | - | Grimsby Town | 0:0 | ||||
| 23. Round | 26/12/2019 | Carlisle United | - | Bradford City | 0:0 |
England