| 5. Round | 26/08/2023 | Port Vale FC | - | Carlisle United | 1:0 | ||||
| 6. Round | 02/09/2023 | Carlisle United | - | Shrewsbury Town | 2:0 | ||||
| 7. Round | 09/09/2023 | Stevenage FC | - | Carlisle United | 2:2 | ||||
| 8. Round | 16/09/2023 | Lincoln City | - | Carlisle United | 1:1 | ||||
| 9. Round | 23/09/2023 | Carlisle United | - | Derby County | 0:2 | ||||
| 10. Round | 30/09/2023 | Wycombe Wanderers | - | Carlisle United | 2:0 |  |
Iceland