| 1. Round | 03/08/2019 | Hartlepool United | - | Sutton United | 1:3 | ||||
| 2. Round | 06/08/2019 | Halifax Town | - | Hartlepool United | 2:0 | ||||
| 3. Round | 10/08/2019 | Maidenhead United | - | Hartlepool United | 0:1 | ||||
| 4. Round | 13/08/2019 | Hartlepool United | - | AFC Fylde | 2:2 | ||||
| 5. Round | 17/08/2019 | Hartlepool United | - | Bromley FC | 2:3 | ||||
| 7. Round | 26/08/2019 | Hartlepool United | - | Wrexham AFC | 4:2 |  |
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| 8. Round | 31/08/2019 | Torquay United | - | Hartlepool United | 1:2 | ||||
| 9. Round | 03/09/2019 | Barrow AFC | - | Hartlepool United | 0:1 | ||||
| 10. Round | 07/09/2019 | Hartlepool United | - | Woking FC | 1:1 | |
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| 11. Round | 14/09/2019 | Dagenham & Redbridge | - | Hartlepool United | 3:1 | ||||
| 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 |
England