Head to Head
| England - Isthmian Premier Division | 2019/11/09 15:00 | Cray Wanderers v Cheshunt | L | 6-1 |
Home History
| England - Isthmian Premier Division | 2021/10/19 18:45 | Horsham v Cheshunt | W | 0-2 |
| England - Isthmian Premier Division | 2021/10/17 14:00 | Kingstonian v Cheshunt | D | 1-1 |
| England - Isthmian Premier Division | 2021/10/12 18:45 | AFC Hornchurch v Cheshunt | W | 0-1 |
| England - Isthmian Premier Division | 2021/10/09 14:00 | Cheshunt v Bognor Regis Town | L | 0-1 |
| England - FA Cup - Qualifikation | 2021/10/02 14:00 | AFC Sudbury v Cheshunt | L | 1-0 |
| England - Isthmian Premier Division | 2021/09/28 18:45 | Cheshunt v Brightlingsea Regent | W | 3-1 |
| England - Isthmian Premier Division | 2021/09/25 14:00 | Cheshunt v Carshalton Ath | L | 1-3 |
| England - FA Cup | 2021/09/18 14:00 | Hitchin v Cheshunt | W | 0-3 |
Away History
| England - Isthmian Premier Division | 2021/10/09 14:00 | Haringey Borough v Cray Wanderers | D | 1-1 |
| England - Isthmian Premier Division | 2021/10/02 14:00 | Carshalton Ath v Cray Wanderers | W | 1-3 |
| England - Isthmian Premier Division | 2021/09/29 18:45 | Cray Wanderers v Wingate & Finchley | L | 3-5 |
| England - Isthmian Premier Division | 2021/09/25 14:00 | Cray Wanderers v Brightlingsea Regent | L | 0-2 |
| England - Isthmian Premier Division | 2021/09/14 18:45 | Corinthian Casuals v Cray Wanderers | L | 4-0 |
| England - Isthmian Premier Division | 2021/09/12 14:00 | Cray Wanderers v Potters Bar Town | L | 0-1 |
| England - FA Cup | 2021/09/04 14:00 | Cray Wanderers v Sutton Common Rovers | L | 1-3 |
| England - Isthmian Premier Division | 2021/08/30 14:00 | Margate v Cray Wanderers | L | 2-1 |