| 1 | Tue 13 Aug 2019 | 2-0 v Torquay UnitedTorquay United 0-2 Maidenhead United | Vanarama National League |
| 2 | Sat 17 Aug 2019 | 4-1 v ChorleyMaidenhead United 4-1 Chorley | Vanarama National League |
| 3 | Sat 24 Aug 2019 | 2-1 v Yeovil TownYeovil Town 1-2 Maidenhead United | Vanarama National League |
| 4 | Tue 8 Oct 2019 | 1-2 v EastleighEastleigh 2-1 Maidenhead United | Vanarama National League |
| 5 | Sat 12 Oct 2019 | 2-1 v Ebbsfleet UnitedEbbsfleet United 1-2 Maidenhead United | Vanarama National League |
| 6 | Sat 26 Oct 2019 | 1-0 v Solihull MoorsMaidenhead United 1-0 Solihull Moors | Vanarama National League |
| 7 | Tue 29 Oct 2019 | 1-1 v AFC FyldeMaidenhead United 1-1 AFC Fylde | Vanarama National League |
| 8 | Sat 2 Nov 2019 | 0-2 v Aldershot TownAldershot Town 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 | Sat 7 Dec 2019 | 2-1 v Dagenham & RedbridgeDagenham & Redbridge 1-2 Maidenhead United | Vanarama National League |
| 15 | Sat 21 Dec 2019 | 1-4 v BarnetMaidenhead United 1-4 Barnet | Vanarama National League |
| 16 | Thu 26 Dec 2019 | 0-3 v Notts CountyNotts County 3-0 Maidenhead United | Vanarama National League |
| 17 | Wed 1 Jan 2020 | 0-0 v Notts CountyMaidenhead United 0-0 Notts County | Vanarama National League |
| 18 | Sat 25 Jan 2020 | 2-0 v EastleighMaidenhead United 2-0 Eastleigh | Vanarama National League |
| 19 | Sat 1 Feb 2020 | 2-0 v Solihull MoorsSolihull Moors 0-2 Maidenhead United | Vanarama National League |
| 20 | Sat 22 Feb 2020 | 1-2 v Aldershot TownMaidenhead United 1-2 Aldershot Town | Vanarama National League |
| 21 | Tue 25 Feb 2020 | 1-3 v Ebbsfleet UnitedMaidenhead United 1-3 Ebbsfleet United | Vanarama National League |
| 22 | Sat 29 Feb 2020 | 0-2 v WokingWoking 2-0 Maidenhead United | Vanarama National League |
| 23 | Sat 7 Mar 2020 | 0-1 v Boreham WoodMaidenhead United 0-1 Boreham Wood | Vanarama National League |
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