| 1 | Sat 3 Aug 2019 | 10-3 v Walton CasualsHeybridge Swifts 0-3 Walton Casuals | Friendly |
| 2 | Sat 17 Aug 2019 | 13-1 v HistonHiston 1-3 Heybridge Swifts | BetVictor Isthmian North Division |
| 3 | Tue 20 Aug 2019 | 11-1 v Coggeshall TownHeybridge Swifts 1-1 Coggeshall Town | BetVictor Isthmian North Division |
| 4 | Sat 24 Aug 2019 | 12-5 v Grays AthleticGrays Athletic 5-2 Heybridge Swifts | Emirates FA Cup Preliminary Round |
| 5 | Mon 26 Aug 2019 | 12-1 v Felixstowe & Walton UnitedFelixstowe & Walton United 1-2 Heybridge Swifts | BetVictor Isthmian North Division |
| 6 | Sat 31 Aug 2019 | 11-2 v Grays AthleticHeybridge Swifts 1-2 Grays Athletic | BetVictor Isthmian North Division |
| 7 | Sat 7 Sep 2019 | 12-2 v Bury TownHeybridge Swifts 2-2 Bury Town | Velocity Trophy Group 1 |
| 8 | Sat 14 Sep 2019 | 11-1 v Dereham TownDereham Town 1-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 9 | Tue 17 Sep 2019 | 13-1 v Hullbridge SportsHullbridge Sports 1-3 Heybridge Swifts | BetVictor Isthmian North Division |
| 10 | Sat 21 Sep 2019 | 132-2 v Felixstowe & Walton UnitedFelixstowe & Walton United 2-2 Heybridge Swifts | Velocity Trophy Group 1 |
| 11 | Sat 28 Sep 2019 | 14-1 v Hertford TownHeybridge Swifts 4-1 Hertford Town | Buildbase FA Trophy Extra Preliminary Round |
| 12 | Tue 1 Oct 2019 | 13-2 v Soham Town RangersHeybridge Swifts 3-2 Soham Town Rangers | BetVictor Isthmian North Division |
| 13 | Sat 5 Oct 2019 | 11-1 v Basildon UnitedBasildon United 1-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 14 | Sat 12 Oct 2019 | 12-0 v Staines TownStaines Town 0-2 Heybridge Swifts | Buildbase FA Trophy Preliminary Round |
| 15 | Tue 15 Oct 2019 | 12-1 v Colchester UnitedHeybridge Swifts 2-1 Colchester United | Essex County Cup Third Round |
| 16 | Sat 19 Oct 2019 | 14-1 v Witham TownHeybridge Swifts 4-1 Witham Town | BetVictor Isthmian North Division |
| 17 | Sat 26 Oct 2019 | 11-2 v Potters Bar TownHeybridge Swifts 1-2 Potters Bar Town | Buildbase FA Trophy First Qualifying Round |
| 18 | Sat 2 Nov 2019 | 10-5 v AveleyAveley 5-0 Heybridge Swifts | BetVictor Isthmian North Division |
| 19 | Sat 9 Nov 2019 | 1 5-1 v RomfordHeybridge Swifts 5-1 Romford | BetVictor Isthmian North Division |
| 20 | Sat 16 Nov 2019 | 12-1 v Cambridge CityCambridge City 1-2 Heybridge Swifts | BetVictor Isthmian North Division |
| 21 | Tue 19 Nov 2019 | 10-1 v AFC SudburyHeybridge Swifts 0-1 AFC Sudbury | BetVictor Isthmian North Division |
| 22 | Sat 30 Nov 2019 | 1 4-2 v Great Wakering RoversHeybridge Swifts 4-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 23 | Tue 3 Dec 2019 | 11-3 v Waltham AbbeyWaltham Abbey 3-1 Heybridge Swifts | Essex County Cup Third Round |
| 24 | Sat 7 Dec 2019 | 12-3 v Canvey IslandHeybridge Swifts 2-3 Canvey Island | BetVictor Isthmian North Division |
| 25 | Thu 26 Dec 2019 | 11-2 v Maldon & TiptreeMaldon & Tiptree 2-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 26 | Wed 1 Jan 2020 | 13-1 v Felixstowe & Walton UnitedHeybridge Swifts 3-1 Felixstowe & Walton United | BetVictor Isthmian North Division |
| 27 | Sat 4 Jan 2020 | 13-2 v Grays AthleticGrays Athletic 2-3 Heybridge Swifts | BetVictor Isthmian North Division |
| 28 | Tue 7 Jan 2020 | 10-3 v TilburyTilbury 3-0 Heybridge Swifts | BetVictor Isthmian North Division |
| 29 | Sat 11 Jan 2020 | 11-0 v Bury TownHeybridge Swifts 1-0 Bury Town | BetVictor Isthmian North Division |
| 30 | Sat 18 Jan 2020 | 12-0 v Witham TownWitham Town 0-2 Heybridge Swifts | BetVictor Isthmian North Division |
| 31 | Sat 25 Jan 2020 | 10-1 v Basildon UnitedHeybridge Swifts 0-1 Basildon United | BetVictor Isthmian North Division |
| 32 | Sat 1 Feb 2020 | 12-0 v Soham Town RangersSoham Town Rangers 0-2 Heybridge Swifts | BetVictor Isthmian North Division |
| 33 | Tue 4 Feb 2020 | 13-2 v Hullbridge SportsHeybridge Swifts 3-2 Hullbridge Sports | BetVictor Isthmian North Division |
| 34 | Sat 8 Feb 2020 | 14-4 v Canvey IslandCanvey Island 4-4 Heybridge Swifts | BetVictor Isthmian North Division |
| 35 | Sat 22 Feb 2020 | 1 1-1 v AveleyHeybridge Swifts 1-1 Aveley | BetVictor Isthmian North Division |
| 36 | Sat 29 Feb 2020 | 11-2 v AFC SudburyAFC Sudbury 2-1 Heybridge Swifts | BetVictor Isthmian North Division |
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