| 1 | 11/8/2018 | 13-2 v Folkestone InvictaFolkestone Invicta 2-3 Enfield Town | Bostik League Premier Division |
| 2 | 14/8/2018 | 12-1 v Bishop's StortfordEnfield Town 2-1 Bishop's Stortford | Bostik League Premier Division |
| 3 | 18/8/2018 | 12-2 v AFC HornchurchEnfield Town 2-2 AFC Hornchurch | Bostik League Premier Division |
| 4 | 21/8/2018 | 11-0 v Canvey IslandCanvey Island 0-1 Enfield Town | Velocity Trophy Preliminary Round |
| 5 | 25/8/2018 | 16-1 v Burgess Hill TownBurgess Hill Town 1-6 Enfield Town | Bostik League Premier Division |
| 6 | 27/8/2018 | 11-1 v Wingate & FinchleyWingate & Finchley 1-1 Enfield Town | Bostik League Premier Division |
| 7 | 1/9/2018 | 11-1 v Dorking WanderersEnfield Town 1-1 Dorking Wanderers | Bostik League Premier Division |
| 8 | 8/9/2018 | 10-3 v Bedford TownEnfield Town 0-3 Bedford Town | Emirates FA Cup First Qualifying Round |
| 9 | 15/9/2018 | 12-2 v LewesLewes 2-2 Enfield Town | Bostik League Premier Division |
| 10 | 22/9/2018 | 12-1 v WareEnfield Town 2-1 Ware | Velocity Trophy Second Round |
| 11 | 29/9/2018 | 16-1 v Corinthian-CasualsCorinthian-Casuals 1-6 Enfield Town | Bostik League Premier Division |
| 12 | 13/10/2018 | 11-2 v MargateMargate 2-1 Enfield Town | Bostik League Premier Division |
| 13 | 16/10/2018 | 10-0 v Brightlingsea RegentEnfield Town 0-0 Brightlingsea Regent | Bostik League Premier Division |
| 14 | 20/10/2018 | 16-0 v WhitehawkEnfield Town 6-0 Whitehawk | Bostik League Premier Division |
| 15 | 23/10/2018 | 12-1 v Tonbridge AngelsTonbridge Angels 1-2 Enfield Town | Bostik League Premier Division |
| 16 | 27/10/2018 | 11-0 v Lowestoft TownLowestoft Town 0-1 Enfield Town | Buildbase FA Trophy First Qualifying Round |
| 17 | 3/11/2018 | 12-2 v Haringey BoroughEnfield Town 2-2 Haringey Borough | Bostik League Premier Division |
| 18 | 6/11/2018 | 11-4 v Hayes & Yeading UnitedHayes & Yeading United 4-1 Enfield Town | Middlesex County Cup Second Round |
| 19 | 10/11/2018 | 11-2 v Basingstoke TownBasingstoke Town 2-1 Enfield Town | Buildbase FA Trophy Second Qualifying Round |
| 20 | 13/11/2018 | 11-4 v WorthingEnfield Town 1-4 Worthing | Bostik League Premier Division |
| 21 | 17/11/2018 | 11-4 v LeatherheadLeatherhead 4-1 Enfield Town | Bostik League Premier Division |
| 22 | 24/11/2018 | 10-1 v KingstonianEnfield Town 0-1 Kingstonian | Bostik League Premier Division |
| 23 | 27/11/2018 | 12-1 v Maldon & TiptreeMaldon & Tiptree 1-2 Enfield Town | Velocity Trophy Third Round |
| 24 | 1/12/2018 | 10-1 v Carshalton AthleticCarshalton Athletic 1-0 Enfield Town | Bostik League Premier Division |
| 25 | 4/12/2018 | 12-1 v Bognor Regis TownBognor Regis Town 1-2 Enfield Town | Bostik League Premier Division |
| 26 | 8/12/2018 | 14-1 v Harlow TownEnfield Town 4-1 Harlow Town | Bostik League Premier Division |
| 27 | 26/12/2018 | 14-1 v Wingate & FinchleyEnfield Town 4-1 Wingate & Finchley | Bostik League Premier Division |
| 28 | 29/12/2018 | 12-1 v Potters Bar TownPotters Bar Town 1-2 Enfield Town | Bostik League Premier Division |
| 29 | 5/1/2019 | 11-1 v LewesEnfield Town 1-1 Lewes | Bostik League Premier Division |
| 30 | 12/1/2019 | 10-1 v MersthamMerstham 1-0 Enfield Town | Bostik League Premier Division |
| 31 | 15/1/2019 | 14-1 v Burgess Hill TownEnfield Town 4-1 Burgess Hill Town | Velocity Trophy Quarter Final |
| 32 | 19/1/2019 | 10-2 v Corinthian-CasualsEnfield Town 0-2 Corinthian-Casuals | Bostik League Premier Division |
| 33 | 22/1/2019 | 10-1 v Dorking WanderersDorking Wanderers 1-0 Enfield Town | Bostik League Premier Division |
| 34 | 26/1/2019 | 13-0 v WorthingWorthing 0-3 Enfield Town | Bostik League Premier Division |
| 35 | 9/2/2019 | 13-1 v Burgess Hill TownEnfield Town 3-1 Burgess Hill Town | Bostik League Premier Division |
| 36 | 12/2/2019 | 13-3 v Bishop's StortfordEnfield Town 3-3 Bishop's Stortford | Velocity Trophy Semi Final |
| 37 | 6/4/2019 | 11-2 v KingstonianKingstonian 2-1 Enfield Town | Bostik League Premier Division |
| 38 | 10/4/2019 | 12-0 v AFC HornchurchAFC Hornchurch 0-2 Enfield Town | Velocity Trophy Final |
| 39 | 13/4/2019 | 10-3 v Carshalton AthleticEnfield Town 0-3 Carshalton Athletic | Bostik League Premier Division |
