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 * |
| |
USSR
Ukraine
Azerbaijan
Armenia
Kazakhstan
Moldova
Austria
England
Belgium
Bulgaria
Hungary
Germany
Netherlands
Georgia
Spain
Italy
Norway
Poland
Portugal
Serbia
Slovenia
France
Croatia
Montenegro
Czech
Sweden
Scotland
Argentina
Canada
China
Australia
