Home History
| 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 |
| 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 |
Away History
| England Isthmian Premier Division | 2019/11/02 15:00 | Cheshunt v Lewes | L | 0-2 |
| England Isthmian Premier Division | 2019/10/19 14:00 | Enfield Town v Cheshunt | L | 2-1 |
| England Isthmian Premier Division | 2019/10/15 18:45 | Folkestone Invicta v Cheshunt | L | 4-2 |
| England Isthmian Premier Division | 2019/10/12 14:00 | Cheshunt v Worthing | L | 1-2 |
| England Isthmian Premier Division | 2019/10/05 14:00 | Leatherhead v Cheshunt | L | 3-0 |
| England Isthmian Premier Division | 2019/10/01 18:45 | Cheshunt v Wingate & Finchley | W | 1-0 |
| England Isthmian Premier Division | 2019/09/28 14:00 | Cheshunt v Horsham | L | 0-1 |
| England FA Cup Qualification | 2019/09/21 14:00 | Maidstone Utd v Cheshunt | L | 4-1 |