| 1 | Sat 10 Aug 2019 | 11-4 v East Thurrock UnitedEast Thurrock United 4-1 Cheshunt |
| 2 | Tue 13 Aug 2019 | 12-0 v Potters Bar TownCheshunt 2-0 Potters Bar Town |
| 3 | Sat 17 Aug 2019 | 10-1 v Haringey BoroughCheshunt 0-1 Haringey Borough |
| 4 | Mon 26 Aug 2019 | 11-1 v Corinthian-CasualsCheshunt 1-1 Corinthian-Casuals |
| 5 | Sat 31 Aug 2019 | 12-3 v Bishop's StortfordBishop's Stortford 3-2 Cheshunt |
| 6 | Sat 14 Sep 2019 | 11-2 v MargateCheshunt 1-2 Margate |
| 7 | Tue 17 Sep 2019 | 12-1 v Bognor Regis TownBognor Regis Town 1-2 Cheshunt |
| 8 | Sat 28 Sep 2019 | 10-1 v HorshamCheshunt 0-1 Horsham |
| 9 | Tue 1 Oct 2019 | 1 1-0 v Wingate & FinchleyCheshunt 1-0 Wingate & Finchley |
| 10 | Sat 5 Oct 2019 | 10-3 v LeatherheadLeatherhead 3-0 Cheshunt |
| 11 | Sat 12 Oct 2019 | 11-2 v WorthingCheshunt 1-2 Worthing |
| 12 | Tue 15 Oct 2019 | 12-4 v Folkestone InvictaFolkestone Invicta 4-2 Cheshunt |
| 13 | Sat 19 Oct 2019 | 11-2 v Enfield TownEnfield Town 2-1 Cheshunt |
| 14 | Sat 2 Nov 2019 | 10-2 v LewesCheshunt 0-2 Lewes |
| 15 | Sat 9 Nov 2019 | 11-6 v Cray WanderersCray Wanderers 6-1 Cheshunt |
| 16 | Sat 16 Nov 2019 | 10-1 v Carshalton AthleticCheshunt 0-1 Carshalton Athletic |
| 17 | Sat 23 Nov 2019 | 13-0 v MersthamCheshunt 3-0 Merstham |
| 18 | Sat 7 Dec 2019 | 10-1 v Bishop's StortfordCheshunt 0-1 Bishop's Stortford |
| 19 | Sat 28 Dec 2019 | 11-3 v Corinthian-CasualsCorinthian-Casuals 3-1 Cheshunt |
| 20 | Sat 4 Jan 2020 | 13-1 v KingstonianCheshunt 3-1 Kingstonian |
| 21 | Sat 11 Jan 2020 | 12-1 v Wingate & FinchleyWingate & Finchley 1-2 Cheshunt |
| 22 | Sat 18 Jan 2020 | 12-3 v Enfield TownCheshunt 2-3 Enfield Town |
| 23 | Sat 25 Jan 2020 | 10-2 v WorthingWorthing 2-0 Cheshunt |
| 24 | Tue 4 Feb 2020 | 10-3 v HornchurchHornchurch 3-0 Cheshunt |
| 25 | Sat 8 Feb 2020 | 16-1 v LewesLewes 1-6 Cheshunt |
| 26 | Sat 22 Feb 2020 | 10-2 v HorshamHorsham 2-0 Cheshunt |
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