Home History
| England Isthmian Premier Division | 2019/12/14 15:00 | Bognor Regis Town v Cray Wanderers | L | 7-2 |
| England Isthmian Premier Division | 2019/12/07 15:00 | Cray Wanderers v Potters Bar Town | W | 4-0 |
| England Isthmian Premier Division | 2019/11/30 15:00 | Carshalton Ath v Cray Wanderers | L | 4-0 |
| England Isthmian Premier Division | 2019/11/16 15:00 | Brightlingsea Regent v Cray Wanderers | W | 0-2 |
| 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 |
Away History
| England Isthmian Premier Division | 2019/12/21 15:00 | Margate v Leatherhead | D | 0-0 |
| England Isthmian Premier Division | 2019/12/14 15:00 | Leatherhead v Brightlingsea Regent | W | 1-0 |
| England Isthmian Premier Division | 2019/12/07 15:00 | Lewes v Leatherhead | W | 0-1 |
| England FA Trophy | 2019/11/23 15:00 | Leatherhead v Dorking Wanderers | L | 0-3 |
| England Isthmian Premier Division | 2019/11/16 15:00 | East Thurrock v Leatherhead | L | 3-0 |
| England Isthmian Premier Division | 2019/11/12 19:45 | Leatherhead v Corinthian Casuals | W | 2-1 |
| England FA Trophy | 2019/11/09 15:00 | Needham Market v Leatherhead | W | 1-2 |
| England Isthmian Premier Division | 2019/11/02 15:00 | Bishop's Stortford v Leatherhead | W | 0-1 |