FA Cup 2023/24, First Qualifying Round |
 | 02.09.2023 |  | Chatham Town | – | Ramsgate | | 1:5 (0:2) |
| Chatham |
FA Cup 2022/23, Second Qualifying Round |
| 20.09.2022 | | Chatham Town | – | Walton & Hersham | | 1:3 (0:1) * |
| Chatham |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Abbey Rangers | – | Chatham Town | | 5:0 (2:0) |
| Addlestone Addlestone Moor |
FA Cup 2020/21, Third Qualifying Round |
| 14.10.2020 | | Havant & Waterlooville | – | Chatham Town | | 4:1 |
| Havant |
FA Cup 2019/20, Extra Preliminary Round |
| 10.08.2019 | | Cray Valley Paper Mills | – | Chatham Town | | 2:1 (2:0) |
| London |
FA Cup 2018/19, Preliminary Round |
| 25.08.2018 | | Ramsgate | – | Chatham Town | | 2:1 (1:0) |
| Ramsgate |
FA Cup 2017/18, Extra Preliminary Round |
| 16.08.2017 | | Littlehampton Town | – | Chatham Town | | 2:1 (1:1) * |
| Littlehampton |
FA Cup 2016/17, Preliminary Round |
| 22.08.2016 | | Chatham Town | – | Walton Casuals | | 1:2 * |
| Chatham |
FA Cup 2015/16, Second Qualifying Round |
| 26.09.2015 | | Chatham Town | – | Eastbourne Town | | 1:2 (1:0) |
| Chatham |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Chatham Town | – | Whyteleafe | | 1:2 |
| Chatham |
FA Cup 2013/14, Fourth Qualifying Round |
| 26.10.2013 | | Chatham Town | – | St Albans City | | 0:2 (0:1) |
| Chatham |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Hastings United | – | Chatham Town | | 3:1 |
| Hastings |
FA Cup 2011/12, First Qualifying Round |
| 17.09.2011 | | Chatham Town | – | Worthing | | 0:1 |
| |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Chertsey Town | – | Chatham Town | | 2:1 |
| |
FA Cup 2009/10, First Qualifying Round |
| 16.09.2009 | | Walton Casuals | – | Chatham Town | | 2:1 * |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Chipstead | – | Chatham Town | | 1:0 |
| |
FA Cup 2007/08, First Qualifying Round |
| 15.09.2007 | | Chatham Town | – | Margate | | 0:3 |
| |
FA Cup 2006/07, Preliminary Round |
| 02.09.2006 | | Winchester City | – | Chatham Town | | 4:3 |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Chatham Town | – | Leatherhead | | 3:4 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Windsor & Eton | – | Chatham Town | | 3:0 * |
| |
FA Cup 2003/04, Preliminary Round |
| | | Chatham Town | – | Andover | | 2:4 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Chatham Town | – | Godalming & Guildford | | 2:3 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Moneyfields | – | Chatham Town | | 4:0 * |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Windsor & Eton | – | Chatham Town | | 1:0 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Chatham Town | – | Newport IOW | | 2:3 |
| |
FA Cup 1998/99, Preliminary Round |
| | | Horsham | – | Chatham Town | | 3:1 * |
| |
FA Cup 1997/98, Preliminary Round |
| | | Chatham Town | – | Banstead Athletic | | 0:7 |
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FA Cup 1996/97, First Qualifying Round |
| | | Chatham Town | – | Burgess Hill Town | | 1:2 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Dulwich Hamlet | – | Chatham Town | | 2:1 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Ashford Town | – | Chatham Town | | 5:0 |
| |
FA Cup 1993/94, Third Qualifying Round |
| | | Chatham Town | – | Kingstonian | | 1:2 |
| |
FA Cup 1992/93, Preliminary Round |
| | | Worthing | – | Chatham Town | | 8:0 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Chatham Town | – | Steyning Town | | 1:3 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Worthing | – | Chatham Town | | 3:0 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Erith & Belvedere | – | Chatham Town | | 5:1 |
| |
FA Cup 1988/89, Preliminary Round |
| | | Chatham Town | – | Dorking | | 1:5 |
| |
FA Cup 1987/88, Second Qualifying Round |
| | | Chatham Town | – | Fisher Athletic | | 0:3 |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Chatham Town | – | Staines Town | | 1:2 |
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FA Cup 1985/86, Preliminary Round |
| | | Southall | – | Chatham Town | | 2:0 * |
| |
FA Cup 1984/85, Preliminary Round |
| | | Chatham Town | – | Metropolitan Police | | 2:3 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Chatham Town | – | Epsom & Ewell | | 1:2 |
| |
FA Cup 1982/83, Third Qualifying Round |
| | | Folkestone | – | Chatham Town | | 5:0 * |
| |
FA Cup 1981/82, Preliminary Round |
| | | Chatham Town | – | Hastings United | | 1:4 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Bromley | – | Chatham Town | | 4:0 |
| |
FA Cup 1979/80, Third Qualifying Round |
| | | Chatham Town | – | Margate | | 0:1 |
| |
FA Cup 1978/79, Second Qualifying Round |
| | | Medway | – | Eastbourne United | | 0:6 * |
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FA Cup 1977/78, First Qualifying Round |
| | | Medway | – | Sutton United | | 0:1 |
| |
FA Cup 1976/77, Preliminary Round |
| | | Rainham Town | – | Medway | | 2:1 * |
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FA Cup 1975/76, First Qualifying Round |
| | | Medway | – | Tunbridge Wells | | 1:3 |
| |
FA Cup 1974/75, Third Qualifying Round |
| | | Maidstone United | – | Medway | | 7:0 |
| |
FA Cup 1973/74, Third Qualifying Round |
| | | Chatham Town | – | Wycombe Wanderers | | 0:7 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Chatham Town | – | Ashford Town | | 0:2 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Canterbury City | – | Chatham Town | | 5:1 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Chatham Town | – | Gravesend & Northfleet | | 1:4 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Chatham Town | – | Canterbury City | | 1:6 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Chatham Town | – | Sittingbourne | | 1:6 |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Tonbridge | – | Chatham Town | | 2:1 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Margate | – | Chatham Town | | 2:1 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Bexley United | – | Chatham Town | | 6:2 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Chatham Town | – | Dartford | | 2:4 |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Bromley | – | Chatham Town | | 4:1 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Gravesend & Northfleet | – | Chatham Town | | 2:1 |
| |
FA Cup 1959/60, Preliminary Round |
| | | Chatham Town | – | Sheppey United | | 0:3 |
| |
FA Cup 1958/59, Preliminary Round |
| | | Erith & Belvedere | – | Chatham Town | | 8:0 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Ramsgate Athletic | – | Chatham Town | | 5:1 |
| |
FA Cup 1956/57, Preliminary Round |
| | | Chatham Town | – | Ramsgate Athletic | | 2:4 |
| |
FA Cup 1955/56, Preliminary Round |
| | | Chatham Town | – | Ramsgate Athletic | | 1:6 |
| |
FA Cup 1954/55, Preliminary Round |
| | | Chatham Town | – | Walton & Hersham | | 0:4 * |
| |
FA Cup 1953/54, Preliminary Round |
| | | Chatham Town | – | Tooting & Mitcham United | | 1:3 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Chatham Town | – | Dover | | 0:6 |
| |
FA Cup 1951/52, Preliminary Round |
| | | Folkestone | – | Chatham Town | | 4:0 |
| |
FA Cup 1950/51, Extra Preliminary Round |
| | | Whitstable | – | Chatham Town | | 1:0 |
| |
FA Cup 1949/50, Preliminary Round |
| | | Canterbury City | – | Chatham Town | | 2:1 |
| |
FA Cup 1948/49, Extra Preliminary Round |
| | | Chatham Town | – | Dover | | 2:3 |
| |
FA Cup 1947/48, Preliminary Round |
| | | Margate | – | Chatham Town | | 3:0 |
| |
FA Cup 1946/47, Preliminary Round |
| | | Chatham | – | Folkestone | | 0:8 |
| |
FA Cup 1928/29, First Round Proper |
| 24.11.1928 | | Norwich City | – | Chatham | | 6:1 |
| |
FA Cup 1927/28, First Round Proper |
| 26.11.1927 | | Kettering Town | – | Chatham | | 2:0 |
| |
FA Cup 1926/27, Second Round Proper |
| 11.12.1926 | | Norwich City | – | Chatham | | 5:0 |
| |
FA Cup 1925/26, First Round Proper |
| 28.11.1925 | | Chatham | – | Sittingbourne | | 0:3 |
| |
FA Cup 1913/14, First Round Proper |
| 10.01.1914 | | Sunderland | – | Chatham | | 9:0 |
| |
FA Cup 1888/89, Third Round Proper |
| 02.03.1889 | | Chatham | – | West Bromwich Albion | | 1:10 |
| |
FA Cup 1887/88, Third Round |
| 26.11.1887 | | Crusaders | – | Chatham | | 4:0 |
| |
FA Cup 1886/87, Third Round |
| 11.12.1886 | | Chatham | – | Old Foresters | | 1:4 |
| |
FA Cup 1885/86, First Round |
| 31.10.1885 | | Chatham | – | Old Carthusians | | 0:2 |
| |
FA Cup 1884/85, Fifth Round |
| 07.02.1885 | | Chatham | – | Old Carthusians | | 0:3 |
| |
FA Cup 1883/84, First Round |
| 03.11.1883 | | Old Westminsters | – | Chatham | | 3:0 |
| |
FA Cup 1882/83, Second Round |
| 02.12.1882 | | Hendon | – | Chatham | | 2:1 |
| |
FA Cup 1947/48, Extra Preliminary Round |
| | | Whitstable | – | Chatham | | +:- |
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