| 4. Round | 14/08/2018 | Maidenhead United | - | Wrexham AFC | 0:2 | ||||
| 5. Round | 18/08/2018 | Hartlepool United | - | Maidenhead United | 2:1 | ||||
| 7. Round | 27/08/2018 | Braintree Town | - | Maidenhead United | 0:2 | ||||
| 8. Round | 01/09/2018 | Maidenhead United | - | Bromley FC | 2:2 | ||||
| 12. Round | 22/09/2018 | Barrow AFC | - | Maidenhead United | 2:0 | ||||
| 14. Round | 29/09/2018 | Maidenhead United | - | Salford City | 0:3 |  |
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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 | ||||
| 18. Round | 30/10/2018 | Havant & Waterlooville | - | Maidenhead United | 7:0 | ||||
| 22. Round | 27/11/2018 | Maidenhead United | - | Ebbsfleet United | 1:1 |  |
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| 20. Round | 01/12/2018 | Maidenhead United | - | Harrogate Town | 1:2 | ||||
| 24. Round | 08/12/2018 | Maidenhead United | - | Hartlepool United | 0:1 | ||||
| 25. Round | 22/12/2018 | Bromley FC | - | Maidenhead United | 1:0 | ||||
| 26. Round | 26/12/2018 | Maidenhead United | - | Aldershot Town | 4:3 | ||||
| 28. Round | 01/01/2019 | Aldershot Town | - | Maidenhead United | 0:0 | |
England