| 1 | Tue 6 Aug 2019 | 21-1 v ChesterfieldMaidenhead United 1-1 Chesterfield | Vanarama National League |
| 2 | Sat 10 Aug 2019 | 20-1 v Hartlepool UnitedMaidenhead United 0-1 Hartlepool United | Vanarama National League |
| 3 | Tue 13 Aug 2019 | 22-0 v Torquay UnitedTorquay United 0-2 Maidenhead United | Vanarama National League |
| 4 | Tue 24 Sep 2019 | 21-2 v Dover AthleticMaidenhead United 1-2 Dover Athletic | Vanarama National League |
| 5 | Sat 12 Oct 2019 | 22-1 v Ebbsfleet UnitedEbbsfleet United 1-2 Maidenhead United | Vanarama National League |
| 6 | Sat 26 Oct 2019 | 21-0 v Solihull MoorsMaidenhead United 1-0 Solihull Moors | Vanarama National League |
| 7 | Tue 29 Oct 2019 | 21-1 v AFC FyldeMaidenhead United 1-1 AFC Fylde | Vanarama National League |
| 8 | Sat 23 Nov 2019 | 22-3 v WokingMaidenhead United 2-3 Woking | Vanarama National League |
| 9 | Tue 26 Nov 2019 | 24-3 v Dover AthleticDover Athletic 3-4 Maidenhead United | Vanarama National League |
| 10 | Sat 30 Nov 2019 | 20-4 v BarrowMaidenhead United 0-4 Barrow | Vanarama National League |
| 11 | Sat 7 Dec 2019 | 22-1 v Dagenham & RedbridgeDagenham & Redbridge 1-2 Maidenhead United | Vanarama National League |
| 12 | Sat 21 Dec 2019 | 21-4 v BarnetMaidenhead United 1-4 Barnet | Vanarama National League |
| 13 | Thu 26 Dec 2019 | 20-3 v Notts CountyNotts County 3-0 Maidenhead United | Vanarama National League |
| 14 | Sat 28 Dec 2019 | 22-0 v WrexhamMaidenhead United 2-0 Wrexham | Vanarama National League |
| 15 | Wed 1 Jan 2020 | 20-0 v Notts CountyMaidenhead United 0-0 Notts County | Vanarama National League |
| 16 | Sat 4 Jan 2020 | 20-1 v Harrogate TownHarrogate Town 1-0 Maidenhead United | Vanarama National League |
| 17 | Sat 25 Jan 2020 | 22-0 v EastleighMaidenhead United 2-0 Eastleigh | Vanarama National League |
| 18 | Sat 22 Feb 2020 | 21-2 v Aldershot TownMaidenhead United 1-2 Aldershot Town | Vanarama National League |
| 19 | Tue 25 Feb 2020 | 21-3 v Ebbsfleet UnitedMaidenhead United 1-3 Ebbsfleet United | Vanarama National League |
| 20 | Sat 29 Feb 2020 | 20-2 v WokingWoking 2-0 Maidenhead United | Vanarama National League |
| 21 | Sat 7 Mar 2020 | 20-1 v Boreham WoodMaidenhead United 0-1 Boreham Wood | Vanarama National League |
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