| 1 | Sat 14 Sep 2019 | 70-4 v HorshamBrightlingsea Regent 0-4 Horsham | BetVictor Isthmian Premier Division |
| 2 | Sat 21 Sep 2019 | 121-2 v East Thurrock UnitedEast Thurrock United 2-1 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 3 | Sat 5 Oct 2019 | 152-3 v Folkestone InvictaFolkestone Invicta 3-2 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 4 | Sat 12 Oct 2019 | 71-1 v Wingate & FinchleyBrightlingsea Regent 1-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 5 | Sat 19 Oct 2019 | 150-3 v WorthingWorthing 3-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 6 | Sat 26 Oct 2019 | 71-2 v Royston TownBrightlingsea Regent 1-2 Royston Town | Buildbase FA Trophy First Qualifying Round |
| 7 | Sat 2 Nov 2019 | 2 0-2 v KingstonianBrightlingsea Regent 0-2 Kingstonian | BetVictor Isthmian Premier Division |
| 8 | Tue 5 Nov 2019 | 20-2 v Bowers & PitseaBowers & Pitsea 2-0 Brightlingsea Regent | Essex County Cup Third Round |
| 9 | Sat 16 Nov 2019 | 2 0-2 v Cray WanderersBrightlingsea Regent 0-2 Cray Wanderers | BetVictor Isthmian Premier Division |
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