| 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 | 26/8/2019 | 1-2 v BromleyMaidenhead United 1-2 Bromley | Vanarama National League |
| 4 | 7/9/2019 | 0-1 v Dagenham & RedbridgeMaidenhead United 0-1 Dagenham & Redbridge | Vanarama National League |
| 5 | 5/10/2019 | 0-1 v FC Halifax TownMaidenhead United 0-1 FC Halifax Town | Vanarama National League |
| 6 | 8/10/2019 | 1-2 v EastleighEastleigh 2-1 Maidenhead United | Vanarama National League |
| 7 | 12/10/2019 | 2-1 v Ebbsfleet UnitedEbbsfleet United 1-2 Maidenhead United | Vanarama National League |
| 8 | 29/10/2019 | 1-1 v AFC FyldeMaidenhead United 1-1 AFC Fylde | Vanarama National League |
| 9 | 2/11/2019 | 0-2 v Aldershot TownAldershot Town 2-0 Maidenhead United | Vanarama National League |
| 10 | 9/11/2019 | 1-3 v Rotherham UnitedMaidenhead United 1-3 Rotherham United | Emirates FA Cup First Round |
| 11 | 16/11/2019 | 1-2 v Boreham WoodBoreham Wood 2-1 Maidenhead United | Vanarama National League |
| 12 | 7/12/2019 | 2-1 v Dagenham & RedbridgeDagenham & Redbridge 1-2 Maidenhead United | Vanarama National League |
| 13 | 28/12/2019 | 2-0 v WrexhamMaidenhead United 2-0 Wrexham | Vanarama National League |
| 14 | 1/1/2020 | 0-0 v Notts CountyMaidenhead United 0-0 Notts County | Vanarama National League |
| 15 | 4/1/2020 | 0-1 v Harrogate TownHarrogate Town 1-0 Maidenhead United | Vanarama National League |
| 16 | 25/1/2020 | 2-0 v EastleighMaidenhead United 2-0 Eastleigh | Vanarama National League |
| 17 | 1/2/2020 | 2-0 v Solihull MoorsSolihull Moors 0-2 Maidenhead United | Vanarama National League |
| 18 | 22/2/2020 | 1-2 v Aldershot TownMaidenhead United 1-2 Aldershot Town | Vanarama National League |
| 19 | 25/2/2020 | 1-3 v Ebbsfleet UnitedMaidenhead United 1-3 Ebbsfleet United | Vanarama National League |
| 20 | 29/2/2020 | 0-2 v WokingWoking 2-0 Maidenhead United | Vanarama National League |
| 21 | 7/3/2020 | 0-1 v Boreham WoodMaidenhead United 0-1 Boreham Wood | Vanarama National League |
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