| 1 | Sat 9 Feb 2019 | 1-1 v AFC FyldeMaidstone United 1-1 AFC Fylde | National League |
| 2 | Tue 19 Feb 2019 | 0-1 v FC Halifax TownMaidstone United 0-1 FC Halifax Town | National League |
| 3 | Sat 23 Feb 2019 | 1-1 v Stockport CountyStockport County 1-1 Maidstone United | Buildbase FA Trophy Fourth Round |
| 4 | Sat 9 Mar 2019 | 2-0 v Havant & WaterloovilleMaidstone United 2-0 Havant & Waterlooville | National League |
| 5 | Tue 12 Mar 2019 | 0-2 v EastleighEastleigh 2-0 Maidstone United | National League |
| 6 | Sat 16 Mar 2019 | 0-1 v WrexhamWrexham 1-0 Maidstone United | National League |
| 7 | Sat 30 Mar 2019 | 2-2 v Harrogate TownHarrogate Town 2-2 Maidstone United | National League |
| 8 | Sat 6 Apr 2019 | 0-2 v Salford CityMaidstone United 0-2 Salford City | National League |
| 9 | Tue 9 Apr 2019 | 2-1 v BarnetMaidstone United 2-1 Barnet | National League |
| 10 | Sat 13 Apr 2019 | 1-4 v ChesterfieldChesterfield 4-1 Maidstone United | National League |
| 11 | Fri 19 Apr 2019 | 0-2 v Braintree TownMaidstone United 0-2 Braintree Town | National League |
| 12 | Sat 27 Apr 2019 | 0-2 v Aldershot TownMaidstone United 0-2 Aldershot Town | National League |
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