| 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 |
