| 1. Round | 04/08/2018 | Braintree Town | - | Halifax Town | 0:2 | ||||
| 2. Round | 07/08/2018 | Barnet FC | - | Braintree Town | 1:1 | ||||
| 3. Round | 11/08/2018 | Chesterfield FC | - | Braintree Town | 1:0 | ||||
| 4. Round | 14/08/2018 | Braintree Town | - | Hartlepool United | 1:1 | ||||
| 9. Round | 04/09/2018 | Dagenham & Redbridge | - | Braintree Town | 1:0 | ||||
| 11. Round | 15/09/2018 | Gateshead FC | - | Braintree Town | 0:1 | ||||
| 13. Round | 25/09/2018 | Braintree Town | - | Leyton Orient | 1:5 | ||||
| 14. Round | 29/09/2018 | AFC Fylde | - | Braintree Town | 3:0 | ||||
| 29. Round | 05/01/2019 | Halifax Town | - | Braintree Town | 0:0 | ||||
| 30. Round | 19/01/2019 | Braintree Town | - | Barnet FC | 4:0 | ||||
| 31. Round | 26/01/2019 | Hartlepool United | - | Braintree Town | 2:1 | ||||
| 35. Round | 23/02/2019 | Braintree Town | - | Aldershot Town | 0:1 | ||||
| 32. Round | 05/03/2019 | Braintree Town | - | Chesterfield FC | 1:3 |
England