Home History
| England FA Cup Qualification | 2019/09/21 14:00 | Moneyfields v Whyteleafe | W | 0-2 |
| England FA Cup Qualification | 2019/09/07 14:00 | Whyteleafe v Merstham | W | 1-0 |
| England Isthmian Division One South | 2019/08/20 18:46 | Chichester City v Whyteleafe | W | 2-3 |
| England FA Cup Qualification | 2018/09/11 18:45 | Whyteleafe v Corinthian Casuals | L | 0-3 |
| England FA Cup Qualification | 2018/09/08 14:00 | Corinthian Casuals v Whyteleafe | D | 0-0 |
| Club Friendly List | 2018/08/04 14:00 | Whyteleafe v Molesey | W | 4-3 |
| Club Friendly List | 2018/07/31 18:45 | Whyteleafe v Kingstonian | L | 1-3 |
| Club Friendly List | 2018/07/28 14:00 | Whyteleafe v South Park | W | 3-1 |
Away History
| England FA Cup Qualification | 2019/09/21 14:00 | Welling v Chipstead | L | 7-0 |
| England FA Cup | 2019/09/07 14:00 | Westfields v Chipstead | W | 0-1 |
| England FA Trophy | 2018/11/13 19:45 | Bedford Town v Chipstead | L | 2-0 |
| England FA Trophy | 2018/11/10 15:00 | Chipstead v Bedford Town | D | 2-2 |
| England Isthmian Cup | 2018/10/30 19:47 | Corinthian Casuals v Chipstead | D | 0-0 |
| England Isthmian Division One South | 2018/10/16 18:46 | Chipstead v Egham | W | 5-0 |
| England Isthmian Cup | 2018/09/04 18:46 | Chipstead v Dorking Wanderers | W | 1-0 |
| England Isthmian Division One South | 2018/03/29 17:38 | Chipstead v South Park | D | 0-0 |
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