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