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