| 1 | Sat 28 Jul 2018 | 144-1 v Dulwich HamletMaidstone United 4-1 Dulwich Hamlet | Friendly |
| 2 | Sat 4 Aug 2018 | 141-1 v Hartlepool UnitedMaidstone United 1-1 Hartlepool United | National League |
| 3 | Tue 7 Aug 2018 | 14 2-1 v Dagenham & RedbridgeDagenham & Redbridge 1-2 Maidstone United | National League |
| 4 | Sat 11 Aug 2018 | 140-3 v FC Halifax TownFC Halifax Town 3-0 Maidstone United | National League |
| 5 | Tue 14 Aug 2018 | 14 1-2 v Leyton OrientMaidstone United 1-2 Leyton Orient | National League |
| 6 | Sat 18 Aug 2018 | 141-0 v BarrowMaidstone United 1-0 Barrow | National League |
| 7 | Sat 25 Aug 2018 | 14 2-3 v Maidenhead UnitedMaidenhead United 3-2 Maidstone United | National League |
| 8 | Mon 27 Aug 2018 | 141-2 v Boreham WoodMaidstone United 1-2 Boreham Wood | National League |
| 9 | Sat 1 Sep 2018 | 140-1 v GatesheadGateshead 1-0 Maidstone United | National League |
| 10 | Tue 4 Sep 2018 | 14 0-1 v Sutton UnitedMaidstone United 0-1 Sutton United | National League |
| 11 | Sat 8 Sep 2018 | 14 0-1 v Salford CitySalford City 1-0 Maidstone United | National League |
| 12 | Sat 22 Sep 2018 | 141-0 v Braintree TownBraintree Town 0-1 Maidstone United | National League |
| 13 | Sun 2 Dec 2018 | 1-0 v Swindon TownSwindon Town 0-1 Woking | Emirates FA Cup Second Round |
| 14 | Sat 8 Dec 2018 | 4-2 v Weston-super-MareWeston-super-Mare 2-4 Woking | National League South |
| 15 | Sun 6 Jan 2019 | 0-2 v WatfordWoking 0-2 Watford | Emirates FA Cup Third Round |
| 16 | Wed 9 Jan 2019 | 2-0 v Welling UnitedWoking 2-0 Welling United | National League South |
| 17 | Sat 9 Feb 2019 | 3-2 v Truro CityBillericay Town 3-2 Truro City | National League South |
| 18 | Sat 16 Feb 2019 | 2-0 v Eastbourne BoroughBillericay Town 2-0 Eastbourne Borough | National League South |
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