| 1 | 17/8/2019 | 8 3-1 v AFC SudburyCoggeshall Town 3-1 AFC Sudbury | BetVictor Isthmian North Division |
| 2 | 20/8/2019 | 7 1-1 v Heybridge SwiftsHeybridge Swifts 1-1 Coggeshall Town | BetVictor Isthmian North Division |
| 3 | 24/8/2019 | 84-0 v CockfostersCockfosters 0-4 Coggeshall Town | Emirates FA Cup Preliminary Round |
| 4 | 26/8/2019 | 82-0 v Great Wakering RoversCoggeshall Town 2-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 5 | 31/8/2019 | 81-0 v Brentwood TownBrentwood Town 0-1 Coggeshall Town | BetVictor Isthmian North Division |
| 6 | 7/9/2019 | 8 1-2 v Basildon UnitedBasildon United 2-1 Coggeshall Town | Emirates FA Cup First Qualifying Round |
| 7 | 14/9/2019 | 7 3-1 v Canvey IslandCoggeshall Town 3-1 Canvey Island | BetVictor Isthmian North Division |
| 8 | 17/9/2019 | 70-0 v Felixstowe & Walton UnitedCoggeshall Town 0-0 Felixstowe & Walton United | BetVictor Isthmian North Division |
| 9 | 21/9/2019 | 72-3 v Cambridge CityCambridge City 3-2 Coggeshall Town | BetVictor Isthmian North Division |
| 10 | 24/9/2019 | 125-1 v AFC SudburyCoggeshall Town 5-1 AFC Sudbury | Velocity Trophy Group 1 |
| 11 | 28/9/2019 | 8 1-2 v Bracknell TownBracknell Town 2-1 Coggeshall Town | Buildbase FA Trophy Extra Preliminary Round |
| 12 | 5/10/2019 | 80-2 v Dereham TownCoggeshall Town 0-2 Dereham Town | BetVictor Isthmian North Division |
| 13 | 8/10/2019 | 72-0 v Heybridge SwiftsHeybridge Swifts 0-2 Coggeshall Town | Velocity Trophy Group 1 |
| 14 | 12/10/2019 | 7 2-2 v Coggeshall TownFelixstowe & Walton United 2-2 Coggeshall Town | Velocity Trophy Group 1 |
| 15 | 19/10/2019 | 82-1 v AveleyAveley 1-2 Coggeshall Town | BetVictor Isthmian North Division |
| 16 | 22/10/2019 | 160-3 v Bury TownBury Town 3-0 Coggeshall Town | Velocity Trophy Group 1 |
| 17 | 26/10/2019 | 71-2 v Waltham AbbeyCoggeshall Town 1-2 Waltham Abbey | Essex County Cup Third Round |
| 18 | 2/11/2019 | 81-0 v Hullbridge SportsHullbridge Sports 0-1 Coggeshall Town | BetVictor Isthmian North Division |
| 19 | 9/11/2019 | 81-1 v TilburyCoggeshall Town 1-1 Tilbury | BetVictor Isthmian North Division |
| 20 | 16/11/2019 | 83-2 v RomfordRomford 2-3 Coggeshall Town | BetVictor Isthmian North Division |
| 21 | 23/11/2019 | 81-1 v Soham Town RangersCoggeshall Town 1-1 Soham Town Rangers | BetVictor Isthmian North Division |
| 22 | 30/11/2019 | 81-1 v Bury TownBury Town 1-1 Coggeshall Town | BetVictor Isthmian North Division |
| 23 | 7/12/2019 | 8 0-0 v Grays AthleticGrays Athletic 0-0 Coggeshall Town | BetVictor Isthmian North Division |
