| 1 | Sat 17 Aug 2019 | 13-1 v AFC SudburyCoggeshall Town 3-1 AFC Sudbury | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 11-1 v Heybridge SwiftsHeybridge Swifts 1-1 Coggeshall Town | BetVictor Isthmian North Division |
| 3 | Sat 24 Aug 2019 | 14-0 v CockfostersCockfosters 0-4 Coggeshall Town | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 12-0 v Great Wakering RoversCoggeshall Town 2-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 5 | Sat 31 Aug 2019 | 11-0 v Brentwood TownBrentwood Town 0-1 Coggeshall Town | BetVictor Isthmian North Division |
| 6 | Sat 7 Sep 2019 | 11-2 v Basildon UnitedBasildon United 2-1 Coggeshall Town | Emirates FA Cup First Qualifying Round |
| 7 | Sat 14 Sep 2019 | 13-1 v Canvey IslandCoggeshall Town 3-1 Canvey Island | BetVictor Isthmian North Division |
| 8 | Tue 17 Sep 2019 | 1 0-0 v Felixstowe & Walton UnitedCoggeshall Town 0-0 Felixstowe & Walton United | BetVictor Isthmian North Division |
| 9 | Sat 21 Sep 2019 | 12-3 v Cambridge CityCambridge City 3-2 Coggeshall Town | BetVictor Isthmian North Division |
| 10 | Sat 28 Sep 2019 | 11-2 v Bracknell TownBracknell Town 2-1 Coggeshall Town | Buildbase FA Trophy Extra Preliminary Round |
| 11 | Sat 5 Oct 2019 | 10-2 v Dereham TownCoggeshall Town 0-2 Dereham Town | BetVictor Isthmian North Division |
| 12 | Tue 8 Oct 2019 | 12-0 v Heybridge SwiftsHeybridge Swifts 0-2 Coggeshall Town | Velocity Trophy Group 1 |
| 13 | Sat 12 Oct 2019 | 12-2 v Felixstowe & Walton UnitedCoggeshall Town 2-2 Felixstowe & Walton United | Velocity Trophy Group 1 |
| 14 | Sat 19 Oct 2019 | 12-1 v AveleyAveley 1-2 Coggeshall Town | BetVictor Isthmian North Division |
| 15 | Sat 26 Oct 2019 | 11-2 v Waltham AbbeyCoggeshall Town 1-2 Waltham Abbey | Essex County Cup Third Round |
| 16 | Sat 2 Nov 2019 | 1 1-0 v Hullbridge SportsHullbridge Sports 0-1 Coggeshall Town | BetVictor Isthmian North Division |
| 17 | Sat 9 Nov 2019 | 11-1 v TilburyCoggeshall Town 1-1 Tilbury | BetVictor Isthmian North Division |
| 18 | Sat 16 Nov 2019 | 13-2 v RomfordRomford 2-3 Coggeshall Town | BetVictor Isthmian North Division |
| 19 | Sat 23 Nov 2019 | 11-1 v Soham Town RangersCoggeshall Town 1-1 Soham Town Rangers | BetVictor Isthmian North Division |
| 20 | Sat 30 Nov 2019 | 11-1 v Bury TownBury Town 1-1 Coggeshall Town | BetVictor Isthmian North Division |
| 21 | Sat 7 Dec 2019 | 10-0 v Grays AthleticGrays Athletic 0-0 Coggeshall Town | BetVictor Isthmian North Division |
| 22 | Sat 28 Dec 2019 | 10-0 v Great Wakering RoversGreat Wakering Rovers 0-0 Coggeshall Town | BetVictor Isthmian North Division |
| 23 | Tue 7 Jan 2020 | 15-1 v HistonCoggeshall Town 5-1 Histon | BetVictor Isthmian North Division |
| 24 | Sat 11 Jan 2020 | 10-0 v Basildon UnitedBasildon United 0-0 Coggeshall Town | BetVictor Isthmian North Division |
| 25 | Sat 25 Jan 2020 | 11-4 v Dereham TownDereham Town 4-1 Coggeshall Town | BetVictor Isthmian North Division |
| 26 | Sat 1 Feb 2020 | 1 2-1 v Cambridge CityCoggeshall Town 2-1 Cambridge City | BetVictor Isthmian North Division |
| 27 | Tue 4 Feb 2020 | 12-2 v Felixstowe & Walton UnitedFelixstowe & Walton United 2-2 Coggeshall Town | BetVictor Isthmian North Division |
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