| 1 | Tue 7 Aug 2018 | 1-1 v BarnetBarnet 1-1 Braintree Town | National League |
| 2 | Sat 11 Aug 2018 | 0-1 v ChesterfieldChesterfield 1-0 Braintree Town | National League |
| 3 | Tue 14 Aug 2018 | 1-1 v Hartlepool UnitedBraintree Town 1-1 Hartlepool United | National League |
| 4 | Sat 18 Aug 2018 | 3-4 v Havant & WaterloovilleBraintree Town 3-4 Havant & Waterlooville | National League |
| 5 | Sat 25 Aug 2018 | 0-1 v BarrowBarrow 1-0 Braintree Town | National League |
| 6 | Mon 27 Aug 2018 | 0-2 v Maidenhead UnitedBraintree Town 0-2 Maidenhead United | National League |
| 7 | Sat 22 Sep 2018 | 1-0 v Braintree TownBraintree Town 0-1 Maidstone United | National League |
| 8 | Sat 3 Nov 2018 | 172-0 v BarnetBarnet 0-2 Maidstone United | National League |
| 9 | Sat 10 Nov 2018 | 172-1 v Macclesfield TownMaidstone United 2-1 Macclesfield Town | Emirates FA Cup First Round |
| 10 | Sat 17 Nov 2018 | 171-1 v WrexhamMaidstone United 1-1 Wrexham | National League |
| 11 | Tue 27 Nov 2018 | 171-3 v EastleighMaidstone United 1-3 Eastleigh | National League |
| 12 | Sat 1 Dec 2018 | 170-2 v Oldham AthleticMaidstone United 0-2 Oldham Athletic | Emirates FA Cup Second Round |
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