| 8. Round | 01/09/2018 | Maidenhead United | - | Bromley FC | 2:2 | ||||
| 9. Round | 04/09/2018 | Maidenhead United | - | Eastleigh FC | 2:0 | ||||
| 10. Round | 08/09/2018 | Barnet FC | - | Maidenhead United | 1:0 | ||||
| 11. Round | 15/09/2018 | Maidenhead United | - | Halifax Town | 3:0 | ||||
| 13. Round | 25/09/2018 | Chesterfield FC | - | Maidenhead United | 1:3 |  |
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| 15. Round | 06/10/2018 | Maidenhead United | - | Leyton Orient | 0:2 | ||||
| 16. Round | 13/10/2018 | Boreham Wood | - | Maidenhead United | 3:1 | ||||
| 17. Round | 27/10/2018 | Maidenhead United | - | AFC Fylde | 0:6 |
England