| 1 | Sat 7 Sep 2019 | 5 1-5 v WareWare 5-1 Leiston | Emirates FA Cup First Qualifying Round |
| 2 | Sat 16 Nov 2019 | 50-2 v Cray WanderersBrightlingsea Regent 0-2 Cray Wanderers | BetVictor Isthmian Premier Division |
| 3 | Mon 18 Nov 2019 | 50-2 v Carshalton AthleticCarshalton Athletic 2-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 4 | Sat 30 Nov 2019 | 31-1 v CheshuntBrightlingsea Regent 1-1 Cheshunt | BetVictor Isthmian Premier Division |
| 5 | Tue 3 Dec 2019 | 32-4 v Potters Bar TownPotters Bar Town 4-2 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 6 | Sat 7 Dec 2019 | 52-1 v Corinthian-CasualsBrightlingsea Regent 2-1 Corinthian-Casuals | BetVictor Isthmian Premier Division |
| 7 | Tue 10 Dec 2019 | 51-0 v HistonBrightlingsea Regent 1-0 Histon | Velocity Trophy |
| 8 | Sat 14 Dec 2019 | 5 0-1 v LeatherheadLeatherhead 1-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 9 | Sat 28 Dec 2019 | 50-3 v HornchurchHornchurch 3-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 10 | Sat 4 Jan 2020 | 50-0 v Folkestone InvictaBrightlingsea Regent 0-0 Folkestone Invicta | BetVictor Isthmian Premier Division |
| 11 | Sat 11 Jan 2020 | 52-2 v Enfield TownEnfield Town 2-2 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 12 | Sat 18 Jan 2020 | 50-3 v WorthingBrightlingsea Regent 0-3 Worthing | BetVictor Isthmian Premier Division |
| 13 | Tue 21 Jan 2020 | 52-1 v Enfield TownEnfield Town 1-2 Brightlingsea Regent | Velocity Trophy |
| 14 | Sat 25 Jan 2020 | 50-0 v Wingate & FinchleyWingate & Finchley 0-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 15 | Tue 28 Jan 2020 | 5 1-0 v Bishop's StortfordBrightlingsea Regent 1-0 Bishop's Stortford | BetVictor Isthmian Premier Division |
| 16 | Sat 1 Feb 2020 | 50-0 v Potters Bar TownBrightlingsea Regent 0-0 Potters Bar Town | BetVictor Isthmian Premier Division |
| 17 | Tue 4 Feb 2020 | 52-3 v Bognor Regis TownBognor Regis Town 3-2 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 18 | Sat 8 Feb 2020 | 5 1-2 v KingstonianKingstonian 2-1 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 19 | Sat 15 Feb 2020 | 51-1 v MargateBrightlingsea Regent 1-1 Margate | BetVictor Isthmian Premier Division |
| 20 | Tue 18 Feb 2020 | 50-7 v Bowers & PitseaBowers & Pitsea 7-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 21 | Sat 22 Feb 2020 | 51-0 v LewesLewes 0-1 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 22 | Sat 7 Mar 2020 | 50-1 v Cray WanderersCray Wanderers 1-0 Brightlingsea Regent | BetVictor Isthmian Premier Division |
| 23 | Tue 10 Mar 2020 | 52-2 v Folkestone InvictaFolkestone Invicta 2-2 Brightlingsea Regent | Velocity Trophy Quarter Final |
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