| 3. Round | 11/08/2018 | Hartlepool United | - | Ebbsfleet United | 0:1 | ||||
| 11. Round | 15/09/2018 | Hartlepool United | - | Eastleigh FC | 1:1 | ||||
| 12. Round | 22/09/2018 | Halifax Town | - | Hartlepool United | 1:2 | ||||
| 20. Round | 18/11/2018 | Hartlepool United | - | Barnet FC | 1:3 | ||||
| 21. Round | 24/11/2018 | Dover Athletic | - | Hartlepool United | 2:1 | ||||
| 22. Round | 27/11/2018 | Hartlepool United | - | AFC Fylde | 1:2 | ||||
| 23. Round | 01/12/2018 | Hartlepool United | - | Dagenham & Redbridge | 1:2 | ||||
| 24. Round | 08/12/2018 | Maidenhead United | - | Hartlepool United | 0:1 | ||||
| 25. Round | 22/12/2018 | Hartlepool United | - | Havant & Waterlooville | 1:1 | ||||
| 26. Round | 26/12/2018 | Gateshead FC | - | Hartlepool United | 2:1 | ||||
| 27. Round | 29/12/2018 | Chesterfield FC | - | Hartlepool United | 1:1 | ||||
| 28. Round | 01/01/2019 | Hartlepool United | - | Gateshead FC | 2:1 | ||||
| 29. Round | 05/01/2019 | Hartlepool United | - | Maidstone United | 1:2 | ||||
| 30. Round | 19/01/2019 | Harrogate Town | - | Hartlepool United | 3:1 | ||||
| 31. Round | 26/01/2019 | Hartlepool United | - | Braintree Town | 2:1 | ||||
| 46. Round | 27/04/2019 | Hartlepool United | - | Salford City | 3:2 |
England