| 1 | 10/11/2018 | 0-4 v PortsmouthMaidenhead United 0-4 Portsmouth | Emirates FA Cup First Round |
| 2 | 24/11/2018 | 1-0 v Sutton UnitedSutton United 0-1 Maidenhead United | National League |
| 3 | 27/11/2018 | 1-1 v Ebbsfleet UnitedMaidenhead United 1-1 Ebbsfleet United | National League |
| 4 | 1/12/2018 | 1-2 v Harrogate TownMaidenhead United 1-2 Harrogate Town | National League |
| 5 | 8/12/2018 | 0-1 v Hartlepool UnitedMaidenhead United 0-1 Hartlepool United | National League |
| 6 | 22/12/2018 | 0-1 v BromleyBromley 1-0 Maidenhead United | National League |
| 7 | 26/12/2018 | 4-3 v Aldershot TownMaidenhead United 4-3 Aldershot Town | National League |
| 8 | 29/12/2018 | 0-1 v Braintree TownMaidenhead United 0-1 Braintree Town | National League |
| 9 | 1/1/2019 | 0-0 v Aldershot TownAldershot Town 0-0 Maidenhead United | National League |
| 10 | 5/1/2019 | 1-0 v GatesheadGateshead 0-1 Maidenhead United | National League |
| 11 | 19/1/2019 | 1-2 v Solihull MoorsMaidenhead United 1-2 Solihull Moors | National League |
| 12 | 26/1/2019 | 0-1 v WrexhamWrexham 1-0 Maidenhead United | National League |
| 13 | 9/2/2019 | 1-0 v Boreham WoodMaidenhead United 1-0 Boreham Wood | National League |
| 14 | 16/2/2019 | 1-0 v Leyton OrientLeyton Orient 0-1 Maidenhead United | National League |
| 15 | 23/2/2019 | 1-0 v Dover AthleticMaidenhead United 1-0 Dover Athletic | National League |
| 16 | 2/3/2019 | 1-2 v AFC FyldeAFC Fylde 2-1 Maidenhead United | National League |
| 17 | 5/3/2019 | 1-1 v Dagenham & RedbridgeMaidenhead United 1-1 Dagenham & Redbridge | National League |
