| 1 | Tue 13 Aug 2019 | 22-0 v Potters Bar TownCheshunt 2-0 Potters Bar Town |
| 2 | Sat 17 Aug 2019 | 20-1 v Haringey BoroughCheshunt 0-1 Haringey Borough |
| 3 | Mon 26 Aug 2019 | 21-1 v Corinthian-CasualsCheshunt 1-1 Corinthian-Casuals |
| 4 | Sat 31 Aug 2019 | 22-3 v Bishop's StortfordBishop's Stortford 3-2 Cheshunt |
| 5 | Sat 14 Sep 2019 | 21-2 v MargateCheshunt 1-2 Margate |
| 6 | Tue 17 Sep 2019 | 22-1 v Bognor Regis TownBognor Regis Town 1-2 Cheshunt |
| 7 | Sat 28 Sep 2019 | 20-1 v HorshamCheshunt 0-1 Horsham |
| 8 | Tue 1 Oct 2019 | 2 1-0 v Wingate & FinchleyCheshunt 1-0 Wingate & Finchley |
| 9 | Sat 5 Oct 2019 | 20-3 v LeatherheadLeatherhead 3-0 Cheshunt |
| 10 | Sat 12 Oct 2019 | 161-2 v WorthingCheshunt 1-2 Worthing |
| 11 | Sat 9 Nov 2019 | 21-6 v Cray WanderersCray Wanderers 6-1 Cheshunt |
| 12 | Sat 16 Nov 2019 | 20-1 v Carshalton AthleticCheshunt 0-1 Carshalton Athletic |
| 13 | Sat 23 Nov 2019 | 23-0 v MersthamCheshunt 3-0 Merstham |
| 14 | Sat 30 Nov 2019 | 2 1-1 v Brightlingsea RegentBrightlingsea Regent 1-1 Cheshunt |
| 15 | Sat 11 Jan 2020 | 22-1 v Wingate & FinchleyWingate & Finchley 1-2 Cheshunt |
| 16 | Sat 18 Jan 2020 | 2 2-3 v Enfield TownCheshunt 2-3 Enfield Town |
| 17 | Sat 25 Jan 2020 | 2 0-2 v WorthingWorthing 2-0 Cheshunt |
| 18 | Tue 28 Jan 2020 | 21-1 v Bowers & PitseaCheshunt 1-1 Bowers & Pitsea |
| 19 | Sat 1 Feb 2020 | 21-3 v LeatherheadCheshunt 1-3 Leatherhead |
| 20 | Tue 4 Feb 2020 | 20-3 v HornchurchHornchurch 3-0 Cheshunt |
| 21 | Sat 22 Feb 2020 | 120-2 v HorshamHorsham 2-0 Cheshunt |
| 22 | Sat 7 Mar 2020 | 2 0-2 v Carshalton AthleticCarshalton Athletic 2-0 Cheshunt |
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