| 1 | Tue 20 Aug 2019 | 21-1 v Heybridge SwiftsHeybridge Swifts 1-1 Coggeshall Town | BetVictor Isthmian North Division |
| 2 | Sat 24 Aug 2019 | 24-0 v CockfostersCockfosters 0-4 Coggeshall Town | Emirates FA Cup Preliminary Round |
| 3 | Mon 26 Aug 2019 | 22-0 v Great Wakering RoversCoggeshall Town 2-0 Great Wakering Rovers | BetVictor Isthmian North Division |
| 4 | Tue 3 Sep 2019 | 51-4 v Maldon & TiptreeMaldon & Tiptree 4-1 Coggeshall Town | Velocity Trophy Group 1 |
| 5 | Sat 7 Sep 2019 | 121-2 v Basildon UnitedBasildon United 2-1 Coggeshall Town | Emirates FA Cup First Qualifying Round |
| 6 | Sat 21 Sep 2019 | 2 2-3 v Cambridge CityCambridge City 3-2 Coggeshall Town | BetVictor Isthmian North Division |
| 7 | Sat 28 Sep 2019 | 21-2 v Bracknell TownBracknell Town 2-1 Coggeshall Town | Buildbase FA Trophy Extra Preliminary Round |
| 8 | Tue 8 Oct 2019 | 122-0 v Heybridge SwiftsHeybridge Swifts 0-2 Coggeshall Town | Velocity Trophy Group 1 |
| 9 | Sat 12 Oct 2019 | 122-2 v Felixstowe & Walton UnitedCoggeshall Town 2-2 Felixstowe & Walton United | Velocity Trophy Group 1 |
| 10 | Tue 22 Oct 2019 | 20-3 v Bury TownBury Town 3-0 Coggeshall Town | Velocity Trophy Group 1 |
| 11 | Sat 26 Oct 2019 | 121-2 v Waltham AbbeyCoggeshall Town 1-2 Waltham Abbey | Essex County Cup Third Round |
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