| 1 | Sat 17 Aug 2019 | 63-1 v HistonHiston 1-3 Heybridge Swifts | BetVictor Isthmian North Division |
| 2 | Tue 20 Aug 2019 | 61-1 v Coggeshall TownHeybridge Swifts 1-1 Coggeshall Town | BetVictor Isthmian North Division |
| 3 | Sat 24 Aug 2019 | 52-5 v Grays AthleticGrays Athletic 5-2 Heybridge Swifts | Emirates FA Cup Preliminary Round |
| 4 | Mon 26 Aug 2019 | 6 2-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-2 Heybridge Swifts | BetVictor Isthmian North Division |
| 5 | Sat 31 Aug 2019 | 61-2 v Grays AthleticHeybridge Swifts 1-2 Grays Athletic | BetVictor Isthmian North Division |
| 6 | Tue 3 Sep 2019 | 62-1 v AFC SudburyAFC Sudbury 1-2 Heybridge Swifts | Velocity Trophy Group 1 |
| 7 | Sat 7 Sep 2019 | 62-2 v Bury TownHeybridge Swifts 2-2 Bury Town | Velocity Trophy Group 1 |
| 8 | Sat 14 Sep 2019 | 6 1-1 v Dereham TownDereham Town 1-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 9 | Tue 17 Sep 2019 | 63-1 v Hullbridge SportsHullbridge Sports 1-3 Heybridge Swifts | BetVictor Isthmian North Division |
| 10 | Sat 21 Sep 2019 | 62-2 v Felixstowe & Walton UnitedFelixstowe & Walton United 2-2 Heybridge Swifts | Velocity Trophy Group 1 |
| 11 | Sat 28 Sep 2019 | 64-1 v Hertford TownHeybridge Swifts 4-1 Hertford Town | Buildbase FA Trophy Extra Preliminary Round |
| 12 | Tue 1 Oct 2019 | 6 3-2 v Soham Town RangersHeybridge Swifts 3-2 Soham Town Rangers | BetVictor Isthmian North Division |
| 13 | Sat 5 Oct 2019 | 61-1 v Basildon UnitedBasildon United 1-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 14 | Sat 12 Oct 2019 | 62-0 v Staines TownStaines Town 0-2 Heybridge Swifts | Buildbase FA Trophy Preliminary Round |
| 15 | Tue 15 Oct 2019 | 62-1 v Colchester UnitedHeybridge Swifts 2-1 Colchester United | Essex County Cup Third Round |
| 16 | Sat 19 Oct 2019 | 64-1 v Witham TownHeybridge Swifts 4-1 Witham Town | BetVictor Isthmian North Division |
| 17 | Sat 26 Oct 2019 | 61-2 v Potters Bar TownHeybridge Swifts 1-2 Potters Bar Town | Buildbase FA Trophy First Qualifying Round |
| 18 | Sat 2 Nov 2019 | 6 0-5 v AveleyAveley 5-0 Heybridge Swifts | BetVictor Isthmian North Division |
| 19 | Sat 16 Nov 2019 | 62-1 v Cambridge CityCambridge City 1-2 Heybridge Swifts | BetVictor Isthmian North Division |
| 20 | Tue 19 Nov 2019 | 6 0-1 v AFC SudburyHeybridge Swifts 0-1 AFC Sudbury | BetVictor Isthmian North Division |
| 21 | Tue 3 Dec 2019 | 61-3 v Waltham AbbeyWaltham Abbey 3-1 Heybridge Swifts | Essex County Cup Third Round |
| 22 | Sat 7 Dec 2019 | 62-3 v Canvey IslandHeybridge Swifts 2-3 Canvey Island | BetVictor Isthmian North Division |
| 23 | Thu 26 Dec 2019 | 61-2 v Maldon & TiptreeMaldon & Tiptree 2-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 24 | Wed 1 Jan 2020 | 53-1 v Felixstowe & Walton UnitedHeybridge Swifts 3-1 Felixstowe & Walton United | BetVictor Isthmian North Division |
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