| 2. Round | 07/08/2018 | Solihull Moors | - | Maidenhead United | 1:0 | ||||
| 3. Round | 11/08/2018 | Dagenham & Redbridge | - | Maidenhead United | 2:2 | ||||
| 4. Round | 14/08/2018 | Maidenhead United | - | Wrexham AFC | 0:2 | ||||
| 7. Round | 27/08/2018 | Braintree Town | - | Maidenhead United | 0:2 | ||||
| 9. Round | 04/09/2018 | Maidenhead United | - | Eastleigh FC | 2:0 |  |
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| 12. Round | 22/09/2018 | Barrow AFC | - | Maidenhead United | 2:0 | ||||
| 13. Round | 25/09/2018 | Chesterfield FC | - | Maidenhead United | 1:3 | ||||
| 14. Round | 29/09/2018 | Maidenhead United | - | Salford City | 0:3 | ||||
| 16. Round | 13/10/2018 | Boreham Wood | - | Maidenhead United | 3:1 | ||||
| 17. Round | 27/10/2018 | Maidenhead United | - | AFC Fylde | 0:6 |  |
England