| 1 | Mon 9 Jul 2018 | 305-1 v St Neots TownSt Neots Town 1-5 Milton Keynes Dons | Friendly |
| 2 | Tue 28 Aug 2018 | 270-3 v AFC BournemouthAFC Bournemouth 3-0 Milton Keynes Dons | Carabao Cup Second Round |
| 3 | Tue 4 Sep 2018 | 273-3 v Peterborough UnitedMilton Keynes Dons 3-3 Peterborough United | Checkatrade Trophy Southern Group H |
| 4 | Tue 20 Nov 2018 | 0-2 v Tranmere RoversOxford City 0-2 Tranmere Rovers | Emirates FA Cup First Round Replay |
| 5 | Sat 19 Jan 2019 | 1-2 v Solihull MoorsMaidenhead United 1-2 Solihull Moors | National League |
| 6 | Sat 26 Jan 2019 | 0-1 v WrexhamWrexham 1-0 Maidenhead United | National League |
| 7 | Sat 9 Feb 2019 | 1-0 v Boreham WoodMaidenhead United 1-0 Boreham Wood | National League |
| 8 | Sat 16 Feb 2019 | 1-0 v Leyton OrientLeyton Orient 0-1 Maidenhead United | National League |
| 9 | Sat 23 Feb 2019 | 1-0 v Dover AthleticMaidenhead United 1-0 Dover Athletic | National League |
| 10 | Sat 2 Mar 2019 | 1-2 v AFC FyldeAFC Fylde 2-1 Maidenhead United | National League |
| 11 | Tue 5 Mar 2019 | 1-1 v Dagenham & RedbridgeMaidenhead United 1-1 Dagenham & Redbridge | National League |
| 12 | Tue 12 Mar 2019 | 0-3 v Ebbsfleet UnitedEbbsfleet United 3-0 Maidenhead United | National League |
| 13 | Sat 16 Mar 2019 | 0-1 v Harrogate TownHarrogate Town 1-0 Maidenhead United | National League |
| 14 | Sat 30 Mar 2019 | 1-0 v FC Halifax TownFC Halifax Town 0-1 Maidenhead United | National League |
| 15 | Sat 6 Apr 2019 | 0-1 v BarnetMaidenhead United 0-1 Barnet | National League |
| 16 | Fri 19 Apr 2019 | 1-1 v BarrowMaidenhead United 1-1 Barrow | National League |
| 17 | Mon 22 Apr 2019 | 0-2 v EastleighEastleigh 2-0 Maidenhead United | National League |
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