| 1 | 10/8/2019 | 41-1 v LewesLewes 1-1 Enfield Town | BetVictor Isthmian Premier Division |
| 2 | 13/8/2019 | 45-0 v Bishop's StortfordEnfield Town 5-0 Bishop's Stortford | BetVictor Isthmian Premier Division |
| 3 | 17/8/2019 | 41-4 v HorshamEnfield Town 1-4 Horsham | BetVictor Isthmian Premier Division |
| 4 | 24/8/2019 | 42-1 v LeatherheadLeatherhead 1-2 Enfield Town | BetVictor Isthmian Premier Division |
| 5 | 26/8/2019 | 42-2 v Potters Bar TownEnfield Town 2-2 Potters Bar Town | BetVictor Isthmian Premier Division |
| 6 | 31/8/2019 | 41-0 v Bowers & PitseaBowers & Pitsea 0-1 Enfield Town | BetVictor Isthmian Premier Division |
| 7 | 7/9/2019 | 4 1-0 v AFC Rushden & DiamondsEnfield Town 1-0 AFC Rushden & Diamonds | Emirates FA Cup First Qualifying Round |
| 8 | 14/9/2019 | 43-1 v Corinthian-CasualsEnfield Town 3-1 Corinthian-Casuals | BetVictor Isthmian Premier Division |
| 9 | 21/9/2019 | 4 2-0 v Braintree TownEnfield Town 2-0 Braintree Town | Emirates FA Cup Second Qualifying Round |
| 10 | 28/9/2019 | 42-0 v MersthamEnfield Town 2-0 Merstham | BetVictor Isthmian Premier Division |
| 11 | 1/10/2019 | 4 2-0 v Brightlingsea RegentBrightlingsea Regent 0-2 Enfield Town | BetVictor Isthmian Premier Division |
| 12 | 5/10/2019 | 40-1 v Chichester CityChichester City 1-0 Enfield Town | Emirates FA Cup Third Qualifying Round |
| 13 | 12/10/2019 | 45-3 v Cray WanderersCray Wanderers 3-5 Enfield Town | BetVictor Isthmian Premier Division |
| 14 | 19/10/2019 | 42-1 v CheshuntEnfield Town 2-1 Cheshunt | BetVictor Isthmian Premier Division |
| 15 | 22/10/2019 | 41-1 v HornchurchEnfield Town 1-1 Hornchurch | BetVictor Isthmian Premier Division |
| 16 | 26/10/2019 | 41-1 v Bishop's StortfordBishop's Stortford 1-1 Enfield Town | Buildbase FA Trophy First Qualifying Round |
| 17 | 29/10/2019 | 44-2 v Bishop's StortfordEnfield Town 4-2 Bishop's Stortford | Buildbase FA Trophy First Qualifying Round |
| 18 | 9/11/2019 | 4 5-0 v Thatcham TownEnfield Town 5-0 Thatcham Town | Buildbase FA Trophy Second Qualifying Round |
| 19 | 16/11/2019 | 41-3 v Folkestone InvictaEnfield Town 1-3 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 20 | 20/11/2019 | 4 0-0 v KingstonianKingstonian 0-0 Enfield Town | BetVictor Isthmian Premier Division |
| 21 | 23/11/2019 | 44-3 v Maldon & TiptreeEnfield Town 4-3 Maldon & Tiptree | Buildbase FA Trophy Third Qualifying Round |
| 22 | 26/11/2019 | 42-1 v Carshalton AthleticEnfield Town 2-1 Carshalton Athletic | BetVictor Isthmian Premier Division |
| 23 | 30/11/2019 | 42-2 v Wingate & FinchleyEnfield Town 2-2 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 24 | 3/12/2019 | 4 1-4 v Bognor Regis TownBognor Regis Town 4-1 Enfield Town | BetVictor Isthmian Premier Division |
| 25 | 7/12/2019 | 40-4 v Bowers & PitseaEnfield Town 0-4 Bowers & Pitsea | BetVictor Isthmian Premier Division |
