| 1 | Tue 3 Sep 2019 | 17 2-1 v AFC SudburyAFC Sudbury 1-2 Heybridge Swifts | Velocity Trophy Group 1 |
| 2 | Sat 14 Sep 2019 | 171-1 v Dereham TownDereham Town 1-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 3 | Tue 17 Sep 2019 | 17 3-1 v Hullbridge SportsHullbridge Sports 1-3 Heybridge Swifts | BetVictor Isthmian North Division |
| 4 | Sat 21 Sep 2019 | 172-2 v Felixstowe & Walton UnitedFelixstowe & Walton United 2-2 Heybridge Swifts | Velocity Trophy Group 1 |
| 5 | Sat 28 Sep 2019 | 174-1 v Hertford TownHeybridge Swifts 4-1 Hertford Town | Buildbase FA Trophy Extra Preliminary Round |
| 6 | Tue 1 Oct 2019 | 173-2 v Soham Town RangersHeybridge Swifts 3-2 Soham Town Rangers | BetVictor Isthmian North Division |
| 7 | Sat 5 Oct 2019 | 171-1 v Basildon UnitedBasildon United 1-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 8 | Tue 8 Oct 2019 | 170-2 v Coggeshall TownHeybridge Swifts 0-2 Coggeshall Town | Velocity Trophy Group 1 |
| 9 | Sat 12 Oct 2019 | 17 2-0 v Staines TownStaines Town 0-2 Heybridge Swifts | Buildbase FA Trophy Preliminary Round |
| 10 | Tue 15 Oct 2019 | 17 2-1 v Colchester UnitedHeybridge Swifts 2-1 Colchester United | Essex County Cup Third Round |
| 11 | Sat 19 Oct 2019 | 174-1 v Witham TownHeybridge Swifts 4-1 Witham Town | BetVictor Isthmian North Division |
| 12 | Sat 26 Oct 2019 | 171-2 v Potters Bar TownHeybridge Swifts 1-2 Potters Bar Town | Buildbase FA Trophy First Qualifying Round |
| 13 | Sat 2 Nov 2019 | 17 0-5 v AveleyAveley 5-0 Heybridge Swifts | BetVictor Isthmian North Division |
| 14 | Sat 9 Nov 2019 | 175-1 v RomfordHeybridge Swifts 5-1 Romford | BetVictor Isthmian North Division |
| 15 | Sat 1 Feb 2020 | 172-0 v Soham Town RangersSoham Town Rangers 0-2 Heybridge Swifts | BetVictor Isthmian North Division |
| 16 | Tue 4 Feb 2020 | 173-2 v Hullbridge SportsHeybridge Swifts 3-2 Hullbridge Sports | BetVictor Isthmian North Division |
| 17 | Sat 8 Feb 2020 | 174-4 v Canvey IslandCanvey Island 4-4 Heybridge Swifts | BetVictor Isthmian North Division |
| 18 | Sat 22 Feb 2020 | 171-1 v AveleyHeybridge Swifts 1-1 Aveley | BetVictor Isthmian North Division |
| 19 | Sat 29 Feb 2020 | 17 1-2 v AFC SudburyAFC Sudbury 2-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 20 | Sat 7 Mar 2020 | 170-1 v Cambridge CityHeybridge Swifts 0-1 Cambridge City | BetVictor Isthmian North Division |
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