FA Cup 2023/24, Extra Preliminary Round |
 | 08.08.2023 | | Peacehaven & Telscombe | – | Chipstead | | 4:1 (3:1) * |
| Peacehaven |
FA Cup 2022/23, Extra Preliminary Round |
| 06.08.2022 | | Chipstead | – | Tunbridge Wells | | 1:2 (1:0) |
| Chipstead |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Phoenix Sports | – | Chipstead | | 2:1 (2:0) |
| Barnehurst |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Welling United | – | Chipstead | | 7:0 (3:0) |
| London |
FA Cup 2018/19, Preliminary Round |
| 25.08.2018 | | Chipstead | – | Corinthian | | 0:1 (0:0) |
| Chipstead |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | AFC Sudbury | – | Chipstead | | 3:0 (1:0) |
| Sudbury |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Slough Town | – | Chipstead | | 6:1 |
| Beaconsfield |
FA Cup 2015/16, Preliminary Round |
| 29.08.2015 | | Chipstead | – | Rochester United | | 0:1 |
| Chipstead |
FA Cup 2014/15, First Qualifying Round |
| 16.09.2014 | | Chipstead | – | Merstham | | 3:4 aet
(2:2) * |
| Chipstead |
FA Cup 2013/14, Third Qualifying Round |
| 12.10.2013 | | Chipstead | – | Bishop's Stortford | | 1:6 (1:1) |
| Chipstead |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Chipstead | – | Maidstone United | | 0:4 |
| Chipstead |
FA Cup 2011/12, Second Qualifying Round |
| 01.10.2011 | | Chipstead | – | Billericay Town | | 0:3 |
| |
FA Cup 2010/11, Second Qualifying Round |
| 28.09.2010 | | Chipstead | – | Needham Market | | 0:2 * |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Chipstead | – | Dartford | | 1:6 |
| |
FA Cup 2008/09, Fourth Qualifying Round |
| 25.10.2008 | | Torquay United | – | Chipstead | | 4:1 |
| |
FA Cup 2007/08, Preliminary Round |
| 01.09.2007 | | Littlehampton Town | – | Chipstead | | 3:2 |
| |
FA Cup 2006/07, Preliminary Round |
| 05.09.2006 | | Chipstead | – | Colliers Wood United | | 1:2 * |
| |
FA Cup 2005/06, Second Qualifying Round |
| 24.09.2005 | | Bromley | – | Chipstead | | 2:1 |
| |
FA Cup 2004/05, Preliminary Round |
| | | Horsham | – | Chipstead | | 3:0 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Chipstead | – | Ringmer | | 1:2 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Chipstead | – | Three Bridges | | 1:3 |
| |
FA Cup 2001/02, Extra Preliminary Round |
| | | Slade Green | – | Chipstead | | 5:1 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Chipstead | – | Ashford Town Middlesex | | 0:1 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Chipstead | – | Tonbridge Angels | | 0:5 |
| |
FA Cup 1998/99, Third Qualifying Round |
| | | Dagenham & Redbridge | – | Chipstead | | 2:0 |
| |
FA Cup 1997/98, Preliminary Round |
| | | Wivenhoe Town | – | Chipstead | | 4:0 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Chipstead | – | Corinthian-Casuals | | 2:4 * |
| |
FA Cup 1995/96, Preliminary Round |
| | | Chipstead | – | Horsham | | 0:4 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Chipstead | – | Tonbridge | | 0:3 * |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Croydon | – | Chipstead | | 4:1 |
| |
FA Cup 1992/93, Preliminary Round |
| | | East Thurrock United | – | Chipstead | | 1:0 |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Dover Athletic | – | Chipstead | | 6:0 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Chipstead | – | Littlehampton Town | | 2:3 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Chipstead | – | Barton Rovers | | 2:3 * |
| |
