| 1 | 4/8/2018 | 11-3 v GatesheadMaidenhead United 1-3 Gateshead | National League |
| 2 | 7/8/2018 | 10-1 v Solihull MoorsSolihull Moors 1-0 Maidenhead United | National League |
| 3 | 11/8/2018 | 12-2 v Dagenham & RedbridgeDagenham & Redbridge 2-2 Maidenhead United | National League |
| 4 | 14/8/2018 | 10-2 v WrexhamMaidenhead United 0-2 Wrexham | National League |
| 5 | 18/8/2018 | 11-2 v Hartlepool UnitedHartlepool United 2-1 Maidenhead United | National League |
| 6 | 25/8/2018 | 13-2 v Maidstone UnitedMaidenhead United 3-2 Maidstone United | National League |
| 7 | 27/8/2018 | 12-0 v Braintree TownBraintree Town 0-2 Maidenhead United | National League |
| 8 | 1/9/2018 | 12-2 v BromleyMaidenhead United 2-2 Bromley | National League |
| 9 | 8/9/2018 | 10-1 v BarnetBarnet 1-0 Maidenhead United | National League |
| 10 | 22/9/2018 | 10-2 v BarrowBarrow 2-0 Maidenhead United | National League |
| 11 | 25/9/2018 | 13-1 v ChesterfieldChesterfield 1-3 Maidenhead United | National League |
| 12 | 29/9/2018 | 10-3 v Salford CityMaidenhead United 0-3 Salford City | National League |
| 13 | 6/10/2018 | 10-2 v Leyton OrientMaidenhead United 0-2 Leyton Orient | National League |
| 14 | 13/10/2018 | 11-3 v Boreham WoodBoreham Wood 3-1 Maidenhead United | National League |
| 15 | 27/10/2018 | 10-6 v AFC FyldeMaidenhead United 0-6 AFC Fylde | National League |
| 16 | 30/10/2018 | 1 0-7 v Havant & WaterloovilleHavant & Waterlooville 7-0 Maidenhead United | National League |
| 17 | 10/11/2018 | 10-4 v PortsmouthMaidenhead United 0-4 Portsmouth | Emirates FA Cup First Round |
| 18 | 24/11/2018 | 11-0 v Sutton UnitedSutton United 0-1 Maidenhead United | National League |
| 19 | 27/11/2018 | 11-1 v Ebbsfleet UnitedMaidenhead United 1-1 Ebbsfleet United | National League |
| 20 | 1/12/2018 | 11-2 v Harrogate TownMaidenhead United 1-2 Harrogate Town | National League |
| 21 | 8/12/2018 | 10-1 v Hartlepool UnitedMaidenhead United 0-1 Hartlepool United | National League |
| 22 | 22/12/2018 | 10-1 v BromleyBromley 1-0 Maidenhead United | National League |
| 23 | 26/12/2018 | 1 4-3 v Aldershot TownMaidenhead United 4-3 Aldershot Town | National League |
| 24 | 29/12/2018 | 10-1 v Braintree TownMaidenhead United 0-1 Braintree Town | National League |
| 25 | 1/1/2019 | 10-0 v Aldershot TownAldershot Town 0-0 Maidenhead United | National League |
| 26 | 5/1/2019 | 11-0 v GatesheadGateshead 0-1 Maidenhead United | National League |
| 27 | 19/1/2019 | 11-2 v Solihull MoorsMaidenhead United 1-2 Solihull Moors | National League |
| 28 | 26/1/2019 | 10-1 v WrexhamWrexham 1-0 Maidenhead United | National League |
| 29 | 9/2/2019 | 11-0 v Boreham WoodMaidenhead United 1-0 Boreham Wood | National League |
| 30 | 16/2/2019 | 11-0 v Leyton OrientLeyton Orient 0-1 Maidenhead United | National League |
| 31 | 23/2/2019 | 11-0 v Dover AthleticMaidenhead United 1-0 Dover Athletic | National League |
| 32 | 2/3/2019 | 11-2 v AFC FyldeAFC Fylde 2-1 Maidenhead United | National League |
| 33 | 5/3/2019 | 11-1 v Dagenham & RedbridgeMaidenhead United 1-1 Dagenham & Redbridge | National League |
| 34 | 9/3/2019 | 11-0 v Sutton UnitedMaidenhead United 1-0 Sutton United | National League |
| 35 | 12/3/2019 | 10-3 v Ebbsfleet UnitedEbbsfleet United 3-0 Maidenhead United | National League |
| 36 | 16/3/2019 | 10-1 v Harrogate TownHarrogate Town 1-0 Maidenhead United | National League |
| 37 | 26/3/2019 | 12-1 v Havant & WaterloovilleMaidenhead United 2-1 Havant & Waterlooville | National League |
| 38 | 30/3/2019 | 11-0 v FC Halifax TownFC Halifax Town 0-1 Maidenhead United | National League |
| 39 | 6/4/2019 | 10-1 v BarnetMaidenhead United 0-1 Barnet | National League |
| 40 | 13/4/2019 | 10-3 v Salford CitySalford City 3-0 Maidenhead United | National League |
| 41 | 19/4/2019 | 11-1 v BarrowMaidenhead United 1-1 Barrow | National League |
| 42 | 22/4/2019 | 10-2 v EastleighEastleigh 2-0 Maidenhead United | National League |
| 43 | 27/4/2019 | 12-0 v ChesterfieldMaidenhead United 2-0 Chesterfield | National League |
