Home History
| England Isthmian Premier Division | 2019/11/02 15:00 | Brightlingsea Regent v Kingstonian | L | 0-2 |
| England FA Trophy | 2019/10/26 13:59 | Brightlingsea Regent v Royston Town | L | 1-2 |
| England Isthmian Premier Division | 2019/10/19 14:00 | Worthing v Brightlingsea Regent | L | 3-0 |
| England Isthmian Premier Division | 2019/10/12 14:00 | Brightlingsea Regent v Wingate & Finchley | D | 1-1 |
| England Isthmian Premier Division | 2019/10/05 14:00 | Folkestone Invicta v Brightlingsea Regent | L | 3-2 |
| England Isthmian Premier Division | 2019/10/01 18:45 | Brightlingsea Regent v Enfield Town | L | 0-2 |
| England Isthmian Premier Division | 2019/09/28 14:00 | Brightlingsea Regent v Lewes | L | 2-3 |
| England Isthmian Premier Division | 2019/09/21 14:00 | East Thurrock v Brightlingsea Regent | L | 2-1 |
Away History
| England Isthmian Premier Division | 2019/11/12 19:45 | Wingate & Finchley v Cray Wanderers | W | 0-1 |
| England Isthmian Premier Division | 2019/11/09 15:00 | Cray Wanderers v Cheshunt | W | 6-1 |
| England Isthmian Premier Division | 2019/11/02 15:00 | Cray Wanderers v Worthing | D | 2-2 |
| Kent Senior Cup | 2019/10/30 19:44 | Cray Wanderers v VCD Athletic | L | 0-2 |
| England Isthmian Premier Division | 2019/10/22 18:45 | Horsham v Cray Wanderers | D | 1-1 |
| England Isthmian Premier Division | 2019/10/19 14:00 | Lewes v Cray Wanderers | W | 2-3 |
| England Isthmian Premier Division | 2019/10/15 18:45 | Merstham v Cray Wanderers | W | 1-2 |
| England Isthmian Premier Division | 2019/10/12 14:00 | Cray Wanderers v Enfield Town | L | 3-5 |