Home History
| England FA Cup Qualification | 2019/10/05 14:00 | Haringey Borough v Cray Wanderers | L | 1-0 |
| England Isthmian Premier Division | 2019/10/02 18:45 | Cray Wanderers v Bowers Pitsea | W | 3-1 |
| England Isthmian Premier Division | 2019/09/28 14:00 | Cray Wanderers v East Thurrock | D | 1-1 |
| England FA Cup | 2019/09/22 14:00 | Cray Wanderers v Soham Town Rangers | W | 5-2 |
| England Isthmian Premier Division | 2019/09/17 18:45 | Bishop's Stortford v Cray Wanderers | W | 1-5 |
| England Isthmian Premier Division | 2019/09/14 14:00 | Cray Wanderers v Haringey Borough | D | 1-1 |
| England FA Cup | 2019/09/08 14:00 | Cray Wanderers v Bedfont Sports | W | 2-1 |
| England Isthmian Premier Division | 2019/08/31 14:00 | Potters Bar Town v Cray Wanderers | D | 1-1 |
Away History
| England FA Cup Qualification | 2019/10/05 14:00 | Chichester City v Enfield Town | L | 1-0 |
| England Isthmian Premier Division | 2019/10/01 18:45 | Brightlingsea Regent v Enfield Town | W | 0-2 |
| England Isthmian Premier Division | 2019/09/28 14:00 | Enfield Town v Merstham | W | 2-0 |
| England FA Cup | 2019/09/21 14:00 | Enfield Town v Braintree Town | W | 2-0 |
| England Isthmian Premier Division | 2019/09/14 14:00 | Enfield Town v Corinthian Casuals | W | 3-1 |
| England FA Cup | 2019/09/07 14:00 | Enfield Town v AFC Rushden & Diamonds | W | 1-0 |
| England Isthmian Premier Division | 2019/08/31 14:00 | Bowers Pitsea v Enfield Town | W | 0-1 |
| England Isthmian Premier Division | 2019/08/26 14:00 | Enfield Town v Potters Bar Town | D | 2-2 |