| 1 | 10/8/2019 | 0-1 v Hartlepool UnitedMaidenhead United 0-1 Hartlepool United | Vanarama National League |
| 2 | 13/8/2019 | 2-0 v Torquay UnitedTorquay United 0-2 Maidenhead United | Vanarama National League |
| 3 | 17/8/2019 | 4-1 v ChorleyMaidenhead United 4-1 Chorley | Vanarama National League |
| 4 | 24/8/2019 | 2-1 v Yeovil TownYeovil Town 1-2 Maidenhead United | Vanarama National League |
| 5 | 7/9/2019 | 0-1 v Dagenham & RedbridgeMaidenhead United 0-1 Dagenham & Redbridge | Vanarama National League |
| 6 | 14/9/2019 | 0-1 v BarnetBarnet 1-0 Maidenhead United | Vanarama National League |
| 7 | 24/9/2019 | 1-2 v Dover AthleticMaidenhead United 1-2 Dover Athletic | Vanarama National League |
| 8 | 28/9/2019 | 0-2 v BarrowBarrow 2-0 Maidenhead United | Vanarama National League |
| 9 | 9/11/2019 | 1-3 v Rotherham UnitedMaidenhead United 1-3 Rotherham United | Emirates FA Cup First Round |
| 10 | 16/11/2019 | 1-2 v Boreham WoodBoreham Wood 2-1 Maidenhead United | Vanarama National League |
| 11 | 23/11/2019 | 2-3 v WokingMaidenhead United 2-3 Woking | Vanarama National League |
| 12 | 26/11/2019 | 4-3 v Dover AthleticDover Athletic 3-4 Maidenhead United | Vanarama National League |
| 13 | 30/11/2019 | 0-4 v BarrowMaidenhead United 0-4 Barrow | Vanarama National League |
| 14 | 26/12/2019 | 0-3 v Notts CountyNotts County 3-0 Maidenhead United | Vanarama National League |
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