| 1 | Tue 6 Aug 2019 | 81-1 v ChesterfieldMaidenhead United 1-1 Chesterfield | Vanarama National League |
| 2 | Mon 26 Aug 2019 | 81-2 v BromleyMaidenhead United 1-2 Bromley | Vanarama National League |
| 3 | Sat 31 Aug 2019 | 83-0 v Sutton UnitedSutton United 0-3 Maidenhead United | Vanarama National League |
| 4 | Tue 3 Sep 2019 | 82-2 v WrexhamWrexham 2-2 Maidenhead United | Vanarama National League |
| 5 | Sat 21 Sep 2019 | 81-1 v Harrogate TownMaidenhead United 1-1 Harrogate Town | Vanarama National League |
| 6 | Sat 28 Sep 2019 | 80-2 v BarrowBarrow 2-0 Maidenhead United | Vanarama National League |
| 7 | Sat 5 Oct 2019 | 80-1 v FC Halifax TownMaidenhead United 0-1 FC Halifax Town | Vanarama National League |
| 8 | Tue 8 Oct 2019 | 81-2 v EastleighEastleigh 2-1 Maidenhead United | Vanarama National League |
| 9 | Sat 26 Oct 2019 | 81-0 v Solihull MoorsMaidenhead United 1-0 Solihull Moors | Vanarama National League |
| 10 | Tue 29 Oct 2019 | 81-1 v AFC FyldeMaidenhead United 1-1 AFC Fylde | Vanarama National League |
| 11 | Sat 2 Nov 2019 | 80-2 v Aldershot TownAldershot Town 2-0 Maidenhead United | Vanarama National League |
| 12 | Sat 9 Nov 2019 | 81-3 v Rotherham UnitedMaidenhead United 1-3 Rotherham United | Emirates FA Cup First Round |
| 13 | Sat 23 Nov 2019 | 82-3 v WokingMaidenhead United 2-3 Woking | Vanarama National League |
| 14 | Sat 7 Dec 2019 | 82-1 v Dagenham & RedbridgeDagenham & Redbridge 1-2 Maidenhead United | Vanarama National League |
| 15 | Sat 21 Dec 2019 | 81-4 v BarnetMaidenhead United 1-4 Barnet | Vanarama National League |
| 16 | Thu 26 Dec 2019 | 80-3 v Notts CountyNotts County 3-0 Maidenhead United | Vanarama National League |
| 17 | Sat 28 Dec 2019 | 82-0 v WrexhamMaidenhead United 2-0 Wrexham | Vanarama National League |
| 18 | Wed 1 Jan 2020 | 80-0 v Notts CountyMaidenhead United 0-0 Notts County | Vanarama National League |
| 19 | Sat 4 Jan 2020 | 80-1 v Harrogate TownHarrogate Town 1-0 Maidenhead United | Vanarama National League |
| 20 | Sat 1 Feb 2020 | 82-0 v Solihull MoorsSolihull Moors 0-2 Maidenhead United | Vanarama National League |
| 21 | Sat 22 Feb 2020 | 81-2 v Aldershot TownMaidenhead United 1-2 Aldershot Town | Vanarama National League |
| 22 | Tue 25 Feb 2020 | 81-3 v Ebbsfleet UnitedMaidenhead United 1-3 Ebbsfleet United | Vanarama National League |
| 23 | Sat 29 Feb 2020 | 80-2 v WokingWoking 2-0 Maidenhead United | Vanarama National League |
| 24 | Sat 7 Mar 2020 | 80-1 v Boreham WoodMaidenhead United 0-1 Boreham Wood | Vanarama National League |
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