| 1 | Sat 10 Aug 2019 | 10-0 v MargateMargate 0-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 2 | Tue 13 Aug 2019 | 1 2-4 v Bowers & PitseaBrightlingsea Regent 2-4 Bowers & Pitsea | BetVictor Isthmian Premier Division |
| 3 | Sat 17 Aug 2019 | 10-0 v MersthamBrightlingsea Regent 0-0 Merstham | BetVictor Isthmian Premier Division |
| 4 | Sat 24 Aug 2019 | 11-5 v Haringey BoroughHaringey Borough 5-1 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 5 | Mon 26 Aug 2019 | 11-0 v HornchurchBrightlingsea Regent 1-0 Hornchurch | BetVictor Isthmian Premier Division |
| 6 | Sat 31 Aug 2019 | 11-0 v Corinthian-CasualsCorinthian-Casuals 0-1 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 7 | Sat 7 Sep 2019 | 10-1 v CheshuntCheshunt 1-0 Brightlingsea Regent | Emirates FA Cup First Qualifying Round |
| 8 | Sat 14 Sep 2019 | 10-4 v HorshamBrightlingsea Regent 0-4 Horsham | BetVictor Isthmian Premier Division |
| 9 | Sat 21 Sep 2019 | 11-2 v East Thurrock UnitedEast Thurrock United 2-1 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 10 | Sat 28 Sep 2019 | 12-3 v LewesBrightlingsea Regent 2-3 Lewes | BetVictor Isthmian Premier Division |
| 11 | Tue 1 Oct 2019 | 10-2 v Enfield TownBrightlingsea Regent 0-2 Enfield Town | BetVictor Isthmian Premier Division |
| 12 | Sat 5 Oct 2019 | 12-3 v Folkestone InvictaFolkestone Invicta 3-2 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 13 | Sat 12 Oct 2019 | 11-1 v Wingate & FinchleyBrightlingsea Regent 1-1 Wingate & Finchley | BetVictor Isthmian Premier Division |
| 14 | Sat 19 Oct 2019 | 10-3 v WorthingWorthing 3-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 15 | Sat 26 Oct 2019 | 11-2 v Royston TownBrightlingsea Regent 1-2 Royston Town | Buildbase FA Trophy First Qualifying Round |
| 16 | Sat 2 Nov 2019 | 10-2 v KingstonianBrightlingsea Regent 0-2 Kingstonian | BetVictor Isthmian Premier Division |
| 17 | Tue 5 Nov 2019 | 10-2 v Bowers & PitseaBowers & Pitsea 2-0 Brightlingsea Regent | Essex County Cup Third Round |
| 18 | Sat 16 Nov 2019 | 10-2 v Cray WanderersBrightlingsea Regent 0-2 Cray Wanderers | BetVictor Isthmian Premier Division |
| 19 | Mon 18 Nov 2019 | 10-2 v Carshalton AthleticCarshalton Athletic 2-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 20 | Sat 30 Nov 2019 | 1 1-1 v CheshuntBrightlingsea Regent 1-1 Cheshunt | BetVictor Isthmian Premier Division |
| 21 | Tue 3 Dec 2019 | 12-4 v Potters Bar TownPotters Bar Town 4-2 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 22 | Sat 28 Dec 2019 | 10-3 v HornchurchHornchurch 3-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 23 | Sat 4 Jan 2020 | 10-0 v Folkestone InvictaBrightlingsea Regent 0-0 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 24 | Sat 11 Jan 2020 | 12-2 v Enfield TownEnfield Town 2-2 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 25 | Sat 18 Jan 2020 | 10-3 v WorthingBrightlingsea Regent 0-3 Worthing | BetVictor Isthmian Premier Division |
| 26 | Tue 21 Jan 2020 | 12-1 v Enfield TownEnfield Town 1-2 Brightlingsea Regent | Velocity Trophy |
| 27 | Sat 25 Jan 2020 | 1 0-0 v Wingate & FinchleyWingate & Finchley 0-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 28 | Tue 28 Jan 2020 | 11-0 v Bishop's StortfordBrightlingsea Regent 1-0 Bishop's Stortford | BetVictor Isthmian Premier Division |
| 29 | Sat 1 Feb 2020 | 10-0 v Potters Bar TownBrightlingsea Regent 0-0 Potters Bar Town | BetVictor Isthmian Premier Division |
| 30 | Tue 4 Feb 2020 | 12-3 v Bognor Regis TownBognor Regis Town 3-2 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 31 | Sat 8 Feb 2020 | 11-2 v KingstonianKingstonian 2-1 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 32 | Sat 15 Feb 2020 | 11-1 v MargateBrightlingsea Regent 1-1 Margate | BetVictor Isthmian Premier Division |
| 33 | Tue 18 Feb 2020 | 1 0-7 v Bowers & PitseaBowers & Pitsea 7-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 34 | Sat 22 Feb 2020 | 1 1-0 v LewesLewes 0-1 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 35 | Sat 7 Mar 2020 | 10-1 v Cray WanderersCray Wanderers 1-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 36 | Tue 10 Mar 2020 | 12-2 v Folkestone InvictaFolkestone Invicta 2-2 Brightlingsea Regent | Velocity Trophy Quarter Final |
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