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