| 1 | 17/8/2019 | 11 3-1 v AFC SudburyCoggeshall Town 3-1 AFC Sudbury | BetVictor Isthmian North Division |
| 2 | 20/8/2019 | 101-1 v Heybridge SwiftsHeybridge Swifts 1-1 Coggeshall Town | BetVictor Isthmian North Division |
| 3 | 24/8/2019 | 44-0 v CockfostersCockfosters 0-4 Coggeshall Town | Emirates FA Cup Preliminary Round |
| 4 | 26/8/2019 | 112-0 v Great Wakering RoversCoggeshall Town 2-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 5 | 31/8/2019 | 111-0 v Brentwood TownBrentwood Town 0-1 Coggeshall Town | BetVictor Isthmian North Division |
| 6 | 7/9/2019 | 41-2 v Basildon UnitedBasildon United 2-1 Coggeshall Town | Emirates FA Cup First Qualifying Round |
| 7 | 14/9/2019 | 83-1 v Canvey IslandCoggeshall Town 3-1 Canvey Island | BetVictor Isthmian North Division |
| 8 | 21/9/2019 | 82-3 v Cambridge CityCambridge City 3-2 Coggeshall Town | BetVictor Isthmian North Division |
| 9 | 24/9/2019 | 45-1 v AFC SudburyCoggeshall Town 5-1 AFC Sudbury | Velocity Trophy Group 1 |
| 10 | 28/9/2019 | 41-2 v Bracknell TownBracknell Town 2-1 Coggeshall Town | Buildbase FA Trophy Extra Preliminary Round |
| 11 | 5/10/2019 | 4 0-2 v Dereham TownCoggeshall Town 0-2 Dereham Town | BetVictor Isthmian North Division |
| 12 | 8/10/2019 | 8 2-0 v Heybridge SwiftsHeybridge Swifts 0-2 Coggeshall Town | Velocity Trophy Group 1 |
| 13 | 19/10/2019 | 72-1 v AveleyAveley 1-2 Coggeshall Town | BetVictor Isthmian North Division |
| 14 | 26/10/2019 | 81-2 v Waltham AbbeyCoggeshall Town 1-2 Waltham Abbey | Essex County Cup Third Round |
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