| 1. Round | 03/08/2019 | Carlisle United | - | Crawley Town | 2:1 | ||||
| 2. Round | 10/08/2019 | Swindon Town | - | Carlisle United | 3:2 |  |
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| 3. Round | 17/08/2019 | Carlisle United | - | Mansfield Town | 0:2 | ||||
| 4. Round | 20/08/2019 | Cheltenham Town | - | Carlisle United | 2:0 | ||||
| 5. Round | 24/08/2019 | Carlisle United | - | Salford City | 2:2 | ||||
| 6. Round | 31/08/2019 | Scunthorpe United | - | Carlisle United | 0:1 | |
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| 7. Round | 07/09/2019 | Carlisle United | - | Exeter City | 1:3 | ||||
| 8. Round | 14/09/2019 | Stevenage FC | - | Carlisle United | 2:3 | |
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| 9. Round | 17/09/2019 | Carlisle United | - | Forest Green Rovers | 0:0 | ||||
| 10. Round | 21/09/2019 | Bradford City | - | Carlisle United | 3:1 | |
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| 11. Round | 28/09/2019 | Carlisle United | - | Oldham Athletic | 1:0 | ||||
| 12. Round | 05/10/2019 | Newport County | - | Carlisle United | 1:0 | ||||
| 13. Round | 12/10/2019 | Carlisle United | - | Crewe Alexandra | 2:4 | ||||
| 16. Round | 26/10/2019 | Leyton Orient | - | Carlisle United | 1:1 | ||||
| 22. Round | 21/12/2019 | Colchester United | - | Carlisle United | 3:0 |
England