| 17. Round | 24/10/2023 | Halifax Town | - | Hartlepool United | 2:1 |  |
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| 18. Round | 28/10/2023 | Hartlepool United | - | Rochdale AFC | 2:3 | ||||
| 19. Round | 11/11/2023 | Hartlepool United | - | Ebbsfleet United | 2:2 | ||||
| 20. Round | 18/11/2023 | York City | - | Hartlepool United | 1:3 | ||||
| 21. Round | 21/11/2023 | Kidderminster Harriers | - | Hartlepool United | 1:1 | |
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| 22. Round | 25/11/2023 | Hartlepool United | - | Bromley FC | 1:4 | |
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| 24. Round | 16/12/2023 | Hartlepool United | - | Chesterfield FC | 0:1 | |
England