| 1 | Wed 31 Jul 2019 | 165-3 v KingstonianGrays Athletic 5-3 Kingstonian | Friendly |
| 2 | Sat 3 Aug 2019 | 102-3 v Metropolitan PoliceMetropolitan Police 3-2 Grays Athletic | Friendly |
| 3 | Sat 10 Aug 2019 | 153-2 v VCD AthleticVCD Athletic 2-3 Grays Athletic | Friendly |
| 4 | Sat 21 Sep 2019 | 111-2 v East Thurrock UnitedEast Thurrock United 2-1 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 5 | Sat 28 Sep 2019 | 82-3 v LewesBrightlingsea Regent 2-3 Lewes | BetVictor Isthmian Premier Division |
| 6 | Tue 1 Oct 2019 | 80-2 v Enfield TownBrightlingsea Regent 0-2 Enfield Town | BetVictor Isthmian Premier Division |
| 7 | Sat 5 Oct 2019 | 42-3 v Folkestone InvictaFolkestone Invicta 3-2 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 8 | Sat 12 Oct 2019 | 41-1 v Wingate & FinchleyBrightlingsea Regent 1-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 9 | Sat 19 Oct 2019 | 40-3 v WorthingWorthing 3-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 10 | Sat 26 Oct 2019 | 141-2 v Royston TownBrightlingsea Regent 1-2 Royston Town | Buildbase FA Trophy First Qualifying Round |
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