| 1 | Tue 6 Aug 2019 | 1-1 v ChesterfieldMaidenhead United 1-1 Chesterfield | Vanarama National League |
| 2 | Sat 10 Aug 2019 | 0-1 v Hartlepool UnitedMaidenhead United 0-1 Hartlepool United | Vanarama National League |
| 3 | Tue 13 Aug 2019 | 2-0 v Torquay UnitedTorquay United 0-2 Maidenhead United | Vanarama National League |
| 4 | Sat 17 Aug 2019 | 4-1 v ChorleyMaidenhead United 4-1 Chorley | Vanarama National League |
| 5 | Sat 24 Aug 2019 | 2-1 v Yeovil TownYeovil Town 1-2 Maidenhead United | Vanarama National League |
| 6 | Mon 26 Aug 2019 | 1-2 v BromleyMaidenhead United 1-2 Bromley | Vanarama National League |
| 7 | Sat 31 Aug 2019 | 3-0 v Sutton UnitedSutton United 0-3 Maidenhead United | Vanarama National League |
| 8 | Tue 3 Sep 2019 | 2-2 v WrexhamWrexham 2-2 Maidenhead United | Vanarama National League |
| 9 | Sat 7 Sep 2019 | 0-1 v Dagenham & RedbridgeMaidenhead United 0-1 Dagenham & Redbridge | Vanarama National League |
| 10 | Sat 14 Sep 2019 | 0-1 v BarnetBarnet 1-0 Maidenhead United | Vanarama National League |
| 11 | Sat 21 Sep 2019 | 1-1 v Harrogate TownMaidenhead United 1-1 Harrogate Town | Vanarama National League |
| 12 | Tue 24 Sep 2019 | 1-2 v Dover AthleticMaidenhead United 1-2 Dover Athletic | Vanarama National League |
| 13 | Sat 28 Sep 2019 | 0-2 v BarrowBarrow 2-0 Maidenhead United | Vanarama National League |
| 14 | Sat 25 Jan 2020 | 2-0 v EastleighMaidenhead United 2-0 Eastleigh | Vanarama National League |
| 15 | Sat 1 Feb 2020 | 2-0 v Solihull MoorsSolihull Moors 0-2 Maidenhead United | Vanarama National League |
| 16 | Sat 22 Feb 2020 | 1-2 v Aldershot TownMaidenhead United 1-2 Aldershot Town | Vanarama National League |
| 17 | Tue 25 Feb 2020 | 1-3 v Ebbsfleet UnitedMaidenhead United 1-3 Ebbsfleet United | Vanarama National League |
| 18 | Sat 29 Feb 2020 | 0-2 v WokingWoking 2-0 Maidenhead United | Vanarama National League |
| 19 | Sat 7 Mar 2020 | 0-1 v Boreham WoodMaidenhead United 0-1 Boreham Wood | Vanarama National League |
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