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