| 23. Round | 15/01/2019 | Maidstone United | - | Maidenhead United | 2:4 |  |
|||
| 30. Round | 19/01/2019 | Maidenhead United | - | Solihull Moors | 1:2 | ||||
| 31. Round | 26/01/2019 | Wrexham AFC | - | Maidenhead United | 1:0 | ||||
| 33. Round | 09/02/2019 | Maidenhead United | - | Boreham Wood | 1:0 | ||||
| 34. Round | 16/02/2019 | Leyton Orient | - | Maidenhead United | 0:1 | ||||
| 35. Round | 23/02/2019 | Maidenhead United | - | Dover Athletic | 1:0 | ||||
| 36. Round | 02/03/2019 | AFC Fylde | - | Maidenhead United | 2:1 | ||||
| 32. Round | 05/03/2019 | Maidenhead United | - | Dagenham & Redbridge | 1:1 | ||||
| 38. Round | 12/03/2019 | Ebbsfleet United | - | Maidenhead United | 3:0 | ||||
| 39. Round | 16/03/2019 | Harrogate Town | - | Maidenhead United | 1:0 | ||||
| 41. Round | 30/03/2019 | Halifax Town | - | Maidenhead United | 0:1 | ||||
| 42. Round | 06/04/2019 | Maidenhead United | - | Barnet FC | 0:1 | ||||
| 44. Round | 19/04/2019 | Maidenhead United | - | Barrow AFC | 1:1 | ||||
| 45. Round | 22/04/2019 | Eastleigh FC | - | Maidenhead United | 2:0 |
England