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