| 1 | Sat 29 Aug 2020 | 11-3 v LeistonLeiston 3-1 Brightlingsea Regent | Friendly |
| 2 | Tue 1 Sep 2020 | 13-2 v Maldon & TiptreeBrightlingsea Regent 3-2 Maldon & Tiptree | Friendly |
| 3 | Sat 5 Sep 2020 | 11-3 v Coggeshall TownBrightlingsea Regent 1-3 Coggeshall Town | Friendly |
| 4 | Sat 12 Sep 2020 | 10-1 v RomfordBrightlingsea Regent 0-1 Romford | Friendly |
| 5 | Sat 19 Sep 2020 | 11-2 v MargateBrightlingsea Regent 1-2 Margate | Isthmian League - Premier Division |
| 6 | Tue 22 Sep 2020 | 11-2 v Bury TownBury Town 2-1 Brightlingsea Regent | Emirates FA Cup First Qualifying Round |
| 7 | Sat 26 Sep 2020 | 12-1 v LewesLewes 1-2 Brightlingsea Regent | Isthmian League - Premier Division |
| 8 | Tue 29 Sep 2020 | 11-2 v Bowers & PitseaBowers & Pitsea 2-1 Brightlingsea Regent | Isthmian League - Premier Division |
| 9 | Sat 3 Oct 2020 | 11-1 v East Thurrock UnitedBrightlingsea Regent 1-1 East Thurrock United | Isthmian League - Premier Division |
| 10 | Sat 17 Oct 2020 | 10-4 v HorshamHorsham 4-0 Brightlingsea Regent | Isthmian League - Premier Division |
| 11 | Tue 20 Oct 2020 | 13-0 v LeatherheadBrightlingsea Regent 3-0 Leatherhead | Isthmian League - Premier Division |
| 12 | Sat 24 Oct 2020 | 11-2 v Folkestone InvictaBrightlingsea Regent 1-2 Folkestone Invicta | Isthmian League - Premier Division |
| 13 | Sat 31 Oct 2020 | 11-4 v Kings LangleyKings Langley 4-1 Brightlingsea Regent | Buildbase FA Trophy Third Qualifying Round |
| 14 | Tue 3 Nov 2020 | 132-3 v Enfield TownEnfield Town 3-2 Brightlingsea Regent | Isthmian League - Premier Division |
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