| 1 | 28/7/2018 | 4-1 v Dulwich HamletMaidstone United 4-1 Dulwich Hamlet | Friendly |
| 2 | 4/8/2018 | 1-1 v Hartlepool UnitedMaidstone United 1-1 Hartlepool United | National League |
| 3 | 7/8/2018 | 2-1 v Dagenham & RedbridgeDagenham & Redbridge 1-2 Maidstone United | National League |
| 4 | 11/8/2018 | 0-3 v FC Halifax TownFC Halifax Town 3-0 Maidstone United | National League |
| 5 | 14/8/2018 | 1-2 v Leyton OrientMaidstone United 1-2 Leyton Orient | National League |
| 6 | 27/8/2018 | 1-2 v Boreham WoodMaidstone United 1-2 Boreham Wood | National League |
| 7 | 1/9/2018 | 0-1 v GatesheadGateshead 1-0 Maidstone United | National League |
| 8 | 4/9/2018 | 0-1 v Sutton UnitedMaidstone United 0-1 Sutton United | National League |
| 9 | 8/9/2018 | 0-1 v Salford CitySalford City 1-0 Maidstone United | National League |
| 10 | 15/9/2018 | 0-2 v Harrogate TownMaidstone United 0-2 Harrogate Town | National League |
| 11 | 22/9/2018 | 1-0 v Braintree TownBraintree Town 0-1 Maidstone United | National League |
| 12 | 29/9/2018 | 1-1 v ChesterfieldMaidstone United 1-1 Chesterfield | National League |
| 13 | 6/10/2018 | 0-1 v BromleyMaidstone United 0-1 Bromley | National League |
| 14 | 13/10/2018 | 0-2 v AFC FyldeAFC Fylde 2-0 Maidstone United | National League |
| 15 | 27/10/2018 | 1-3 v Solihull MoorsMaidstone United 1-3 Solihull Moors | National League |
| 16 | 30/10/2018 | 1-1 v Ebbsfleet UnitedEbbsfleet United 1-1 Maidstone United | National League |
| 17 | 3/11/2018 | 2-0 v BarnetBarnet 0-2 Maidstone United | National League |
| 18 | 10/11/2018 | 2-1 v Macclesfield TownMaidstone United 2-1 Macclesfield Town | Emirates FA Cup First Round |
| 19 | 17/11/2018 | 1-1 v WrexhamMaidstone United 1-1 Wrexham | National League |
| 20 | 24/11/2018 | 2-5 v Havant & WaterloovilleHavant & Waterlooville 5-2 Maidstone United | National League |
| 21 | 27/11/2018 | 1-3 v EastleighMaidstone United 1-3 Eastleigh | National League |
| 22 | 1/12/2018 | 0-2 v Oldham AthleticMaidstone United 0-2 Oldham Athletic | Emirates FA Cup Second Round |
