| 1 | 27/10/2018 | 1-3 v Solihull MoorsMaidstone United 1-3 Solihull Moors | National League |
| 2 | 30/10/2018 | 1-1 v Ebbsfleet UnitedEbbsfleet United 1-1 Maidstone United | National League |
| 3 | 3/11/2018 | 2-0 v BarnetBarnet 0-2 Maidstone United | National League |
| 4 | 10/11/2018 | 2-1 v Macclesfield TownMaidstone United 2-1 Macclesfield Town | Emirates FA Cup First Round |
| 5 | 17/11/2018 | 1-1 v WrexhamMaidstone United 1-1 Wrexham | National League |
| 6 | 24/11/2018 | 2-5 v Havant & WaterloovilleHavant & Waterlooville 5-2 Maidstone United | National League |
| 7 | 27/11/2018 | 1-3 v EastleighMaidstone United 1-3 Eastleigh | National League |
| 8 | 1/12/2018 | 0-2 v Oldham AthleticMaidstone United 0-2 Oldham Athletic | Emirates FA Cup Second Round |
| 9 | 8/12/2018 | 0-1 v BarrowBarrow 1-0 Maidstone United | National League |
| 10 | 29/12/2018 | 1-0 v Boreham WoodBoreham Wood 0-1 Maidstone United | National League |
| 11 | 1/1/2019 | 0-1 v Dover AthleticMaidstone United 0-1 Dover Athletic | National League |
| 12 | 15/1/2019 | 2-4 v Maidenhead UnitedMaidstone United 2-4 Maidenhead United | National League |
| 13 | 19/1/2019 | 0-3 v Dagenham & RedbridgeMaidstone United 0-3 Dagenham & Redbridge | National League |
| 14 | 26/1/2019 | 0-3 v Leyton OrientLeyton Orient 3-0 Maidstone United | National League |
| 15 | 9/2/2019 | 1-1 v AFC FyldeMaidstone United 1-1 AFC Fylde | National League |
| 16 | 16/2/2019 | 0-2 v BromleyBromley 2-0 Maidstone United | National League |
| 17 | 19/2/2019 | 0-1 v FC Halifax TownMaidstone United 0-1 FC Halifax Town | National League |
| 18 | 23/2/2019 | 1-1 v Stockport CountyStockport County 1-1 Maidstone United | Buildbase FA Trophy Fourth Round |
| 19 | 9/3/2019 | 2-0 v Havant & WaterloovilleMaidstone United 2-0 Havant & Waterlooville | National League |
| 20 | 12/3/2019 | 0-2 v EastleighEastleigh 2-0 Maidstone United | National League |
| 21 | 6/4/2019 | 0-2 v Salford CityMaidstone United 0-2 Salford City | National League |
| 22 | 9/4/2019 | 2-1 v BarnetMaidstone United 2-1 Barnet | National League |
| 23 | 13/4/2019 | 1-4 v ChesterfieldChesterfield 4-1 Maidstone United | National League |
| 24 | 19/4/2019 | 0-2 v Braintree TownMaidstone United 0-2 Braintree Town | National League |
| 25 | 22/4/2019 | 2-2 v Sutton UnitedSutton United 2-2 Maidstone United | National League |
| 26 | 27/4/2019 | 0-2 v Aldershot TownMaidstone United 0-2 Aldershot Town | National League |
