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