Head to Head
| England Isthmian Premier Division | 2025/02/15 15:00 | Cray Wanderers v Cheshunt | W | 2-1 |
| England Isthmian Premier Division | 2024/10/26 14:00 | Cheshunt v Cray Wanderers | W | 0-1 |
| England Isthmian Premier Division | 2024/02/17 15:00 | Cheshunt v Cray Wanderers | W | 0-1 |
| England Isthmian Premier Division | 2023/09/23 14:00 | Cray Wanderers v Cheshunt | W | 2-1 |
| England Isthmian Premier Division | 2022/03/05 15:00 | Cray Wanderers v Cheshunt | D | 1-1 |
| England Isthmian Premier Division | 2021/10/23 14:00 | Cheshunt v Cray Wanderers | L | 4-0 |
| England Isthmian Premier Division | 2019/11/09 15:00 | Cray Wanderers v Cheshunt | W | 6-1 |
Home History
| England Isthmian Premier Division | 2025/10/18 14:00 | Chatham Town v Cray Wanderers | D | 3-3 |
| England Isthmian Premier Division | 2025/10/11 14:00 | Dulwich v Cray Wanderers | D | 1-1 |
| England FA Trophy | 2025/10/04 14:00 | Bishop's Stortford v Cray Wanderers | L | 4-0 |
| England Isthmian Premier Division | 2025/09/30 18:45 | Cray Wanderers v Dulwich | W | 4-2 |
| England Isthmian Premier Division | 2025/09/27 14:00 | Ramsgate v Cray Wanderers | D | 1-1 |
| England Isthmian Premier Division | 2025/09/20 14:00 | Cray Wanderers v Hashtag United | W | 4-3 |
| England Isthmian Premier Division | 2025/09/13 14:00 | Carshalton Ath v Cray Wanderers | D | 2-2 |
| England Isthmian Premier Division | 2025/09/06 14:00 | Lewes v Cray Wanderers | D | 2-2 |
Away History
| England Isthmian Premier Division | 2025/10/18 14:00 | Cheshunt v Wingate & Finchley | L | 2-3 |
| England Isthmian Premier Division | 2025/10/14 18:45 | Billericay Town v Cheshunt | D | 1-1 |
| England Isthmian Premier Division | 2025/10/11 14:00 | Cheshunt v Cray Valley Paper Mills | D | 1-1 |
| England FA Trophy | 2025/10/04 14:00 | Carshalton Ath v Cheshunt | W | 1-2 |
| England Isthmian Premier Division | 2025/09/27 14:00 | Dartford v Cheshunt | L | 2-0 |
| England Isthmian Premier Division | 2025/09/20 14:00 | Cheshunt v Dulwich | D | 1-1 |
| England Isthmian Premier Division | 2025/09/09 18:45 | Cheshunt v Billericay Town | D | 2-2 |
| England Isthmian Premier Division | 2025/09/06 14:00 | Cheshunt v Burgess Hill Town | D | 1-1 |
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