| 2. Ronde | 10.08.2019 | Swindon Town | - | Carlisle United | 3:2 |  |
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| 4. Ronde | 20.08.2019 | Cheltenham Town | - | Carlisle United | 2:0 | ||||
| 6. Ronde | 31.08.2019 | Scunthorpe United | - | Carlisle United | 0:1 | ||||
| 7. Ronde | 07.09.2019 | Carlisle United | - | Exeter City | 1:3 |  |
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| 8. Ronde | 14.09.2019 | Stevenage FC | - | Carlisle United | 2:3 | ||||
| 9. Ronde | 17.09.2019 | Carlisle United | - | Forest Green Rovers | 0:0 | ||||
| 10. Ronde | 21.09.2019 | Bradford City | - | Carlisle United | 3:1 | ||||
| 11. Ronde | 28.09.2019 | Carlisle United | - | Oldham Athletic | 1:0 | ||||
| 12. Ronde | 05.10.2019 | Newport County | - | Carlisle United | 1:0 | ||||
| 13. Ronde | 12.10.2019 | Carlisle United | - | Crewe Alexandra | 2:4 | ||||
| 14. Ronde | 19.10.2019 | Plymouth Argyle | - | Carlisle United | 2:0 | ||||
| 16. Ronde | 26.10.2019 | Leyton Orient | - | Carlisle United | 1:1 | |
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| 17. Ronde | 02.11.2019 | Carlisle United | - | Macclesfield Town | 2:1 | ||||
| 21. Ronde | 14.12.2019 | Carlisle United | - | Grimsby Town | 0:0 | ||||
| 23. Ronde | 26.12.2019 | Carlisle United | - | Bradford City | 0:0 | ||||
| 24. Ronde | 29.12.2019 | Walsall FC | - | Carlisle United | 1:2 | ||||
| 25. Ronde | 01.01.2020 | Crewe Alexandra | - | Carlisle United | 4:1 | |
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