| 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 | 25/1/2020 | 2-0 v EastleighMaidenhead United 2-0 Eastleigh | Vanarama National League |
| 15 | 1/2/2020 | 2-0 v Solihull MoorsSolihull Moors 0-2 Maidenhead United | Vanarama National League |
| 16 | 22/2/2020 | 1-2 v Aldershot TownMaidenhead United 1-2 Aldershot Town | Vanarama National League |
| 17 | 25/2/2020 | 1-3 v Ebbsfleet UnitedMaidenhead United 1-3 Ebbsfleet United | Vanarama National League |
| 18 | 29/2/2020 | 0-2 v WokingWoking 2-0 Maidenhead United | Vanarama National League |
| 19 | 7/3/2020 | 0-1 v Boreham WoodMaidenhead United 0-1 Boreham Wood | Vanarama National League |
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