FA Cup 2024/25, First Qualifying Round |
 | 31.08.2024 |  | Ashford Town | – | Herne Bay | | 0:2 (0:2) |
| Ashford |
FA Cup 2023/24, Preliminary Round |
| 19.08.2023 | | Redhill | – | Ashford Town | | 1:0 (0:0) |
| Redhill |
FA Cup 2022/23, First Qualifying Round |
| 03.09.2022 | | Ashford Town | – | Westfield | | 2:4 (0:1) |
| Ashford |
FA Cup 2021/22, Second qualifying round |
| 18.09.2021 | | Ashford Town | – | Folkestone Invicta | | 2:7 (2:3) |
| Ashford |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Southall | – | Ashford Town | | 2:1 |
| London |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Sutton Athletic | – | Ashford Town | | 6:0 (2:0) |
| Sutton-at-Hone |
FA Cup 2018/19, Preliminary Round |
| 26.08.2018 | | Cray Valley Paper Mills | – | Ashford Town | | 4:1 (2:0) |
| London |
FA Cup 2017/18, Third Qualifying Round |
| 30.09.2017 | | Ashford Town | – | Leatherhead | | 1:2 (1:1) |
| Ashford |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Herne Bay | – | Ashford Town | | 3:1 |
| Herne Bay |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Hampton & Richmond Borough | – | Ashford Town | | 4:2 |
| London |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Burnham | – | Ashford Town | | 2:1 |
| |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Ashford Town | – | Erith Town | | -:+ |
| |
FA Cup 2009/10, First Qualifying Round |
| 12.09.2009 | | Leatherhead | – | Ashford Town | | 2:0 |
| |
FA Cup 2008/09, First Qualifying Round |
| 14.09.2008 | | Kingstonian | – | Ashford Town | | 3:0 |
| |
FA Cup 2007/08, Preliminary Round |
| 31.08.2007 | | Erith & Belvedere | – | Ashford Town | | 2:0 |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Ashford Town | – | Tonbridge Angels | | 1:3 |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Ashford Town | – | Windsor & Eton | | 0:3 |
| |
FA Cup 2004/05, Preliminary Round |
| | | AFC Wimbledon | – | Ashford Town | | 3:0 |
| |
FA Cup 2003/04, First Qualifying Round |
| | | Bromley | – | Ashford Town | | 1:0 * |
| |
FA Cup 2002/03, Preliminary Round |
| | | Ashford Town | – | Carshalton Athletic | | 1:3 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Hassocks | – | Ashford Town | | 3:2 |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Ashford Town | – | Bracknell Town | | 1:2 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Ashford Town | – | Fisher Athletic | | 0:2 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Grays Athletic | – | Ashford Town | | 2:0 |
| |
FA Cup 1997/98, Fourth Qualifying Round |
| | | Heybridge Swifts | – | Ashford Town | | 5:2 |
| |
FA Cup 1996/97, Second Round Proper |
| 07.12.1996 | | Watford | – | Ashford Town | | 5:0 (0:0) |
| Watford |
FA Cup 1995/96, First Round Proper |
| 21.11.1995 | | Ashford Town | – | Bognor Regis Town | | 0:1 (0:0) * |
| |
FA Cup 1994/95, First Round Proper |
| 22.11.1994 | | Fulham | – | Ashford Town | | 5:3 (2:1) * |
| London |
FA Cup 1993/94, First Qualifying Round |
| | | Kingstonian | – | Ashford Town | | 2:1 |
| |
FA Cup 1992/93, Fourth Qualifying Round |
| | | Ashford Town | – | Slough Town | | 1:2 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Whyteleafe | – | Ashford Town | | 2:0 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Dover Athletic | – | Ashford Town | | 1:0 |
| |
FA Cup 1989/90, Second Qualifying Round |
| | | Ashford Town | – | Erith & Belvedere | | 0:1 |
| |
FA Cup 1988/89, Third Qualifying Round |
| | | Dover Athletic | – | Ashford Town | | 3:0 |
| |
FA Cup 1987/88, First Qualifying Round |
| | | Bromley | – | Ashford Town | | 5:2 |
| |
FA Cup 1986/87, Second Qualifying Round |
| | | Southwick | – | Ashford Town | | 1:0 * |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Hythe Town | – | Ashford Town | | 1:0 |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Ashford Town | – | Lewes | | 1:2 |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| | | Barking | – | Ashford Town | | 3:0 |
| |
FA Cup 1982/83, Preliminary Round |
| | | Ashford Town | – | Sheppey United | | 0:2 |
| |
FA Cup 1981/82, Third Qualifying Round |
| | | Dover | – | Ashford Town | | 2:1 |
| |
FA Cup 1980/81, Third Qualifying Round |
| | | Epsom & Ewell | – | Ashford Town | | 1:0 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Ashford Town | – | Croydon | | 0:2 |
| |
FA Cup 1978/79, Preliminary Round |
| | | Eastbourne United | – | Ashford Town | | 1:0 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Lewes | – | Ashford Town | | 1:0 |
| |
FA Cup 1976/77, Second Qualifying Round |
| | | Ashford Town | – | Hastings United | | 0:1 |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Crawley Town | – | Ashford Town | | 4:1 |
| |
FA Cup 1974/75, First Round Proper |
| 27.11.1974 | | Ashford Town | – | Walsall | | 1:3 |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Ashford Town | – | Maidstone United | | 0:2 * |
| |
FA Cup 1972/73, Fourth Qualifying Round |
| | | Ashford Town | – | Guildford City | | 3:4 |
| |
FA Cup 1971/72, Third Qualifying Round |
| | | Ashford Town | – | Dover | | 0:2 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Herne Bay | – | Ashford Town | | 2:1 |
| |
FA Cup 1969/70, Fourth Qualifying Round |
| | | Ashford Town | – | Walton & Hersham | | 0:1 |
| |
FA Cup 1968/69, Third Qualifying Round |
| | | Ashford Town | – | Canterbury City | | 3:4 |
| |
FA Cup 1967/68, Fourth Qualifying Round |
| | | Wimbledon | – | Ashford Town | | 3:0 |
| |
FA Cup 1966/67, Second Round Proper |
| 10.01.1967 | | Swindon Town | – | Ashford Town | | 5:0 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Tunbridge Wells Rangers | – | Ashford Town | | 4:1 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Deal Town | – | Ashford Town | | 4:2 * |
| |
FA Cup 1963/64, Fourth Qualifying Round |
| | | Folkestone | – | Ashford Town | | 3:0 |
| |
FA Cup 1962/63, Fourth Qualifying Round |
| | | Margate | – | Ashford Town | | 2:0 |
| |
FA Cup 1961/62, Second Round Proper |
| 25.11.1961 | | Ashford Town | – | Queens Park Rangers | | 0:3 |
| |
FA Cup 1960/61, First Round Proper |
| 05.11.1960 | | Ashford Town | – | Gillingham | | 1:2 |
| |
FA Cup 1959/60, First Round Proper |
| 14.11.1959 | | Brentford | – | Ashford Town | | 5:0 |
| |
FA Cup 1958/59, First Round Proper |
| 15.11.1958 | | Ashford Town | – | Crystal Palace | | 0:1 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Gravesend & Northfleet | – | Ashford Town | | 3:1 |
| |
FA Cup 1956/57, First Qualifying Round |
| | | Ashford Town | – | Canterbury City | | 1:2 |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Ashford Town | – | Ramsgate Athletic | | 2:5 |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Snowdown Colliery Welfare | – | Ashford Town | | 5:0 * |
| |
FA Cup 1953/54, Third Qualifying Round |
| | | Hastings United | – | Ashford Town | | 2:1 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Ashford Town | – | Hastings United | | 1:3 |
| |
FA Cup 1951/52, Third Qualifying Round |
| | | Tonbridge | – | Ashford Town | | 4:0 * |
| |
FA Cup 1950/51, First Qualifying Round |
| | | Betteshanger Colliery Welfare | – | Ashford | | 2:1 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Sheppey United | – | Ashford | | 1:0 |
| |
FA Cup 1948/49, First Qualifying Round |
| | | Ramsgate Athletic | – | Ashford | | 4:0 |
| |
FA Cup 1947/48, First Qualifying Round |
| | | Gravesend & Northfleet | – | Ashford | | 4:0 |
| |
FA Cup 1946/47, Second Qualifying Round |
| | | Gravesend & Northfleet | – | Ashford | | 3:2 * |
| |
FA Cup 1934/35, First Round Proper |
| 24.11.1934 | | Ashford | – | Clapton Orient | | 1:4 |
| |
