FA Cup 2021/22, Preliminary Round |
 | 21.08.2021 | | Chipstead | – | Faversham Town | | 3:0 (0:0) |
| Chipstead |
FA Cup 2020/21, Second Qualifying Round |
| 03.10.2020 | | Chipstead | – | East Grinstead Town | | 1:0 |
| Chipstead |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Ramsgate | – | Chipstead | | 0:3 |
| Ramsgate |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Westfield | – | Chipstead | | 0:1 (0:0) |
| Woking |
FA Cup 2019/20, Preliminary Round |
| 03.09.2019 | | Hassocks | – | Chipstead | | 2:3 (0:1) * |
| Hassocks |
FA Cup 2017/18, First Qualifying Round |
| 05.09.2017 | | Chipstead | – | Littlehampton Town | | 4:0 (3:0) * |
| Chipstead |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Chipstead | – | Horley Town | | 2:0 (0:0) |
| Chipstead |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | Chipstead | – | Beckenham Town | | 2:1 |
| Chipstead |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Ashford United | – | Chipstead | | 0:1 |
| Ashford |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Chertsey Town | – | Chipstead | | 1:2 |
| Chertsey |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Hassocks | – | Chipstead | | 1:2 |
| Hassocks |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Chipstead | – | Rye United | | 3:2 |
| Chipstead |
FA Cup 2012/13, Preliminary Round |
| 25.08.2012 | | Chipstead | – | Crowborough Athletic | | 5:2 |
| Chipstead |
FA Cup 2011/12, First Qualifying Round |
| 17.09.2011 | | Chipstead | – | Redhill | | 3:1 |
| |
FA Cup 2011/12, Preliminary Round |
| 04.09.2011 | | Epsom & Ewell | – | Chipstead | | 1:2 |
| |
FA Cup 2010/11, First Qualifying Round |
| 11.09.2010 | | Cobham | – | Chipstead | | 0:1 |
| |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Chipstead | – | Whyteleafe | | 4:3 |
| |
FA Cup 2009/10, Preliminary Round |
| 29.08.2009 | | Burgess Hill Town | – | Chipstead | | 2:3 |
| |
FA Cup 2008/09, Third Qualifying Round |
| 14.10.2008 | | Chipstead | – | Atherstone Town | | 3:0 * |
| |
FA Cup 2008/09, Second Qualifying Round |
| 27.09.2008 | | Dunstable Town | – | Chipstead | | 2:3 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Chipstead | – | Chatham Town | | 1:0 |
| |
FA Cup 2008/09, Preliminary Round |
| 02.09.2008 | | Chipstead | – | Herne Bay | | 2:0 aet
(0:0) * |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Three Bridges | – | Chipstead | | 1:3 |
| |
FA Cup 2005/06, Preliminary Round |
| 27.08.2005 | | Chipstead | – | Brockenhurst | | 4:2 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Whitstable Town | – | Chipstead | | 1:2 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Bedfont | – | Chipstead | | 0:2 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Chipstead | – | Redhill | | 2:0 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Chichester City | – | Chipstead | | 1:3 |
| |
