| 1 | Tue 6 Aug 2019 | 1-1 v ChesterfieldMaidenhead United 1-1 Chesterfield | Vanarama National League |
| 2 | Sat 10 Aug 2019 | 0-1 v Hartlepool UnitedMaidenhead United 0-1 Hartlepool United | Vanarama National League |
| 3 | Tue 13 Aug 2019 | 2-0 v Torquay UnitedTorquay United 0-2 Maidenhead United | Vanarama National League |
| 4 | Sat 17 Aug 2019 | 4-1 v ChorleyMaidenhead United 4-1 Chorley | Vanarama National League |
| 5 | Sat 24 Aug 2019 | 2-1 v Yeovil TownYeovil Town 1-2 Maidenhead United | Vanarama National League |
| 6 | Sat 31 Aug 2019 | 3-0 v Sutton UnitedSutton United 0-3 Maidenhead United | Vanarama National League |
| 7 | Tue 3 Sep 2019 | 2-2 v WrexhamWrexham 2-2 Maidenhead United | Vanarama National League |
| 8 | Sat 7 Sep 2019 | 0-1 v Dagenham & RedbridgeMaidenhead United 0-1 Dagenham & Redbridge | Vanarama National League |
| 9 | Sat 14 Sep 2019 | 0-1 v BarnetBarnet 1-0 Maidenhead United | Vanarama National League |
| 10 | Sat 21 Sep 2019 | 1-1 v Harrogate TownMaidenhead United 1-1 Harrogate Town | Vanarama National League |
| 11 | Tue 24 Sep 2019 | 1-2 v Dover AthleticMaidenhead United 1-2 Dover Athletic | Vanarama National League |
| 12 | Sat 28 Sep 2019 | 0-2 v BarrowBarrow 2-0 Maidenhead United | Vanarama National League |
| 13 | Sat 5 Oct 2019 | 0-1 v FC Halifax TownMaidenhead United 0-1 FC Halifax Town | Vanarama National League |
| 14 | Sat 26 Oct 2019 | 1-0 v Solihull MoorsMaidenhead United 1-0 Solihull Moors | Vanarama National League |
| 15 | Tue 29 Oct 2019 | 1-1 v AFC FyldeMaidenhead United 1-1 AFC Fylde | Vanarama National League |
| 16 | Sat 2 Nov 2019 | 0-2 v Aldershot TownAldershot Town 2-0 Maidenhead United | Vanarama National League |
| 17 | Sat 9 Nov 2019 | 1-3 v Rotherham UnitedMaidenhead United 1-3 Rotherham United | Emirates FA Cup First Round |
| 18 | Sat 16 Nov 2019 | 1-2 v Boreham WoodBoreham Wood 2-1 Maidenhead United | Vanarama National League |
| 19 | Sat 23 Nov 2019 | 2-3 v WokingMaidenhead United 2-3 Woking | Vanarama National League |
| 20 | Tue 26 Nov 2019 | 4-3 v Dover AthleticDover Athletic 3-4 Maidenhead United | Vanarama National League |
| 21 | Sat 30 Nov 2019 | 0-4 v BarrowMaidenhead United 0-4 Barrow | Vanarama National League |
| 22 | Sat 7 Dec 2019 | 2-1 v Dagenham & RedbridgeDagenham & Redbridge 1-2 Maidenhead United | Vanarama National League |
| 23 | Sat 21 Dec 2019 | 1-4 v BarnetMaidenhead United 1-4 Barnet | Vanarama National League |
| 24 | Thu 26 Dec 2019 | 0-3 v Notts CountyNotts County 3-0 Maidenhead United | Vanarama National League |
| 25 | Sat 4 Jan 2020 | 0-1 v Harrogate TownHarrogate Town 1-0 Maidenhead United | Vanarama National League |
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