| 24. Round | 08/12/2018 | Barrow AFC | - | Maidstone United | 1:0 | ||||
| 25. Round | 22/12/2018 | Maidstone United | - | Gateshead FC | 2:3 | ||||
| 26. Round | 26/12/2018 | Dover Athletic | - | Maidstone United | 3:1 |  |
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| 28. Round | 01/01/2019 | Maidstone United | - | Dover Athletic | 0:1 | ||||
| 29. Round | 05/01/2019 | Hartlepool United | - | Maidstone United | 1:2 | ||||
| 23. Round | 15/01/2019 | Maidstone United | - | Maidenhead United | 2:4 | ||||
| 30. Round | 19/01/2019 | Maidstone United | - | Dagenham & Redbridge | 0:3 | ||||
| 31. Round | 26/01/2019 | Leyton Orient | - | Maidstone United | 3:0 | ||||
| 34. Round | 16/02/2019 | Bromley FC | - | Maidstone United | 2:0 | ||||
| 32. Round | 19/02/2019 | Maidstone United | - | Halifax Town | 0:1 |
England