| 1 | Tue 1 Sep 2020 | 143-2 v Maldon & TiptreeBrightlingsea Regent 3-2 Maldon & Tiptree | Friendly |
| 2 | Sat 5 Sep 2020 | 21-3 v Coggeshall TownBrightlingsea Regent 1-3 Coggeshall Town | Friendly |
| 3 | Sat 12 Sep 2020 | 120-1 v RomfordBrightlingsea Regent 0-1 Romford | Friendly |
| 4 | Sat 19 Sep 2020 | 121-2 v MargateBrightlingsea Regent 1-2 Margate | Isthmian League - Premier Division |
| 5 | Tue 22 Sep 2020 | 21-2 v Bury TownBury Town 2-1 Brightlingsea Regent | Emirates FA Cup First Qualifying Round |
| 6 | Sat 3 Oct 2020 | 21-1 v East Thurrock UnitedBrightlingsea Regent 1-1 East Thurrock United | Isthmian League - Premier Division |
| 7 | Tue 6 Oct 2020 | 20-2 v Corinthian-CasualsCorinthian-Casuals 2-0 Brightlingsea Regent | Isthmian League - Premier Division |
| 8 | Sat 10 Oct 2020 | 20-3 v Haringey BoroughBrightlingsea Regent 0-3 Haringey Borough | Isthmian League - Premier Division |
| 9 | Tue 20 Oct 2020 | 23-0 v LeatherheadBrightlingsea Regent 3-0 Leatherhead | Isthmian League - Premier Division |
| 10 | Sat 24 Oct 2020 | 2 1-2 v Folkestone InvictaBrightlingsea Regent 1-2 Folkestone Invicta | Isthmian League - Premier Division |
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