| 1 | 19/10/2019 | 21-2 v Enfield TownEnfield Town 2-1 Cheshunt | BetVictor Isthmian Premier Division |
| 2 | 26/10/2019 | 21-2 v East Thurrock UnitedCheshunt 1-2 East Thurrock United | Buildbase FA Trophy First Qualifying Round |
| 3 | 2/11/2019 | 20-2 v LewesCheshunt 0-2 Lewes | BetVictor Isthmian Premier Division |
| 4 | 16/11/2019 | 120-1 v Carshalton AthleticCheshunt 0-1 Carshalton Athletic | BetVictor Isthmian Premier Division |
| 5 | 23/11/2019 | 123-0 v MersthamCheshunt 3-0 Merstham | BetVictor Isthmian Premier Division |
| 6 | 30/11/2019 | 121-1 v Brightlingsea RegentBrightlingsea Regent 1-1 Cheshunt | BetVictor Isthmian Premier Division |
| 7 | 7/12/2019 | 20-1 v Bishop's StortfordCheshunt 0-1 Bishop's Stortford | BetVictor Isthmian Premier Division |
