| 1 | Sat 3 Aug 2019 | 40-3 v Walton CasualsHeybridge Swifts 0-3 Walton Casuals | Friendly |
| 2 | Sat 31 Aug 2019 | 141-2 v Grays AthleticHeybridge Swifts 1-2 Grays Athletic | BetVictor Isthmian North Division |
| 3 | Tue 3 Sep 2019 | 82-1 v AFC SudburyAFC Sudbury 1-2 Heybridge Swifts | Velocity Trophy Group 1 |
| 4 | Sat 7 Sep 2019 | 42-2 v Bury TownHeybridge Swifts 2-2 Bury Town | Velocity Trophy Group 1 |
| 5 | Sat 14 Sep 2019 | 41-1 v Dereham TownDereham Town 1-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 6 | Sat 28 Sep 2019 | 144-1 v Hertford TownHeybridge Swifts 4-1 Hertford Town | Buildbase FA Trophy Extra Preliminary Round |
| 7 | Tue 1 Oct 2019 | 153-2 v Soham Town RangersHeybridge Swifts 3-2 Soham Town Rangers | BetVictor Isthmian North Division |
| 8 | Sat 5 Oct 2019 | 161-1 v Basildon UnitedBasildon United 1-1 Heybridge Swifts | BetVictor Isthmian North Division |
| 9 | Tue 8 Oct 2019 | 40-2 v Coggeshall TownHeybridge Swifts 0-2 Coggeshall Town | Velocity Trophy Group 1 |
| 10 | Tue 15 Oct 2019 | 42-1 v Colchester UnitedHeybridge Swifts 2-1 Colchester United | Essex County Cup Third Round |
| 11 | Sat 19 Oct 2019 | 154-1 v Witham TownHeybridge Swifts 4-1 Witham Town | BetVictor Isthmian North Division |
| 12 | Sat 9 Nov 2019 | 85-1 v RomfordHeybridge Swifts 5-1 Romford | BetVictor Isthmian North Division |
| 13 | Sat 16 Nov 2019 | 42-1 v Cambridge CityCambridge City 1-2 Heybridge Swifts | BetVictor Isthmian North Division |
| 14 | Tue 19 Nov 2019 | 40-1 v AFC SudburyHeybridge Swifts 0-1 AFC Sudbury | BetVictor Isthmian North Division |
| 15 | Sat 30 Nov 2019 | 74-2 v Great Wakering RoversHeybridge Swifts 4-2 Great Wakering Rovers | BetVictor Isthmian North Division |
| 16 | Tue 3 Dec 2019 | 41-3 v Waltham AbbeyWaltham Abbey 3-1 Heybridge Swifts | Essex County Cup Third Round |
| 17 | Thu 26 Dec 2019 | 41-2 v Maldon & TiptreeMaldon & Tiptree 2-1 Heybridge Swifts | BetVictor Isthmian North Division |
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