| 1. Round | 03/08/2019 | Hartlepool United | - | Sutton United | 1:3 | ||||
| 12. Round | 21/09/2019 | Hartlepool United | - | Dover Athletic | 0:2 |  |
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| 13. Round | 24/09/2019 | Hartlepool United | - | Chesterfield FC | 1:1 | |
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| 14. Round | 28/09/2019 | Eastleigh FC | - | Hartlepool United | 1:1 | ||||
| 15. Round | 05/10/2019 | Hartlepool United | - | Yeovil Town | 2:1 | ||||
| 16. Round | 09/10/2019 | Stockport County | - | Hartlepool United | 2:1 | ||||
| 23. Round | 26/11/2019 | Chesterfield FC | - | Hartlepool United | 1:5 | ||||
| 25. Round | 07/12/2019 | Woking FC | - | Hartlepool United | 2:1 | ||||
| 28. Round | 28/12/2019 | Hartlepool United | - | Barrow AFC | 2:2 | |
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| 29. Round | 01/01/2020 | Hartlepool United | - | Harrogate Town | 0:1 |
England