FA Cup 2023/24, First Round Proper |
 | 04.11.2023 |  | Chesham United | – | Maidstone United | | 0:2 (0:1) |
| Chesham |
FA Cup 2022/23, Second Qualifying Round |
| 20.09.2022 | | Bracknell Town | – | Chesham United | | 3:0 (0:0) * |
| Bracknell Larges Lane |
FA Cup 2021/22, Second qualifying round |
| 18.09.2021 | | Chertsey Town | – | Chesham United | | 1:0 (1:0) |
| Chertsey |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Chesham United | – | Hampton & Richmond Borough | | 1:2 (1:1) |
| Chesham |
FA Cup 2018/19, Second Qualifying Round |
| 22.09.2018 | | Welling United | – | Chesham United | | 2:1 (1:1) |
| London |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Needham Market | – | Chesham United | | 2:0 (1:0) |
| Needham Market |
FA Cup 2016/17, First Round Proper |
| 05.11.2016 | | Peterborough United | – | Chesham United | | 2:1 (1:0) |
| Peterborough |
FA Cup 2015/16, Second Round Proper |
| 06.12.2015 | | Bradford City | – | Chesham United | | 4:0 (2:0) |
| Bradford |
FA Cup 2014/15, First Qualifying Round |
| 16.09.2014 | | Chesham United | – | Dunstable Town | | 1:2 (0:0) * |
| Chesham |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Chesham United | – | Royston Town | | 1:2 |
| Chesham |
FA Cup 2012/13, First Qualifying Round |
| 08.09.2012 | | Chesham United | – | Northwood | | 0:1 (0:0) |
| Chesham |
FA Cup 2011/12, Second Qualifying Round |
| 01.10.2011 | | Dunstable Town | – | Chesham United | | 2:1 (1:0) |
| |
FA Cup 2010/11, Second Qualifying Round |
| 27.09.2010 | | Wealdstone | – | Chesham United | | 4:1 * |
| |
FA Cup 2009/10, Third Qualifying Round |
| 10.10.2009 | | Aylesbury | – | Chesham United | | 4:3 |
| |
FA Cup 2008/09, Third Qualifying Round |
| 11.10.2008 | | Oxford City | – | Chesham United | | 2:1 (0:0) |
| |
FA Cup 2007/08, Second Qualifying Round |
| 02.10.2007 | | Stotfold | – | Chesham United | | 2:1 * |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Chesham United | – | Cheshunt | | 2:3 |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Chesham United | – | Brackley Town | | 0:1 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Bedford Town | – | Chesham United | | 4:1 * |
| |
FA Cup 2003/04, Third Qualifying Round |
| | | Chesham United | – | Weston-Super-Mare | | 1:2 * |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Walton & Hersham | – | Chesham United | | 1:0 |
| |
FA Cup 2001/02, Third Qualifying Round |
| | | Chesham United | – | Cambridge City | | 0:1 (0:0) |
| |
FA Cup 2000/01, Fourth Qualifying Round |
| | | Chesham United | – | Kettering Town | | 0:2 (0:2) |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Chesham United | – | Baldock Town | | 1:3 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Bromley | – | Chesham United | | 2:1 |
| |
FA Cup 1997/98, Second Qualifying Round |
| | | Braintree Town | – | Chesham United | | 3:0 |
| |
FA Cup 1996/97, Third Qualifying Round |
| | | Hayes | – | Chesham United | | 1:0 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Purfleet | – | Chesham United | | 3:1 |
| |
FA Cup 1994/95, First Round Proper |
| 12.11.1994 | | Chesham United | – | Bashley | | 0:1 (0:0) |
| |
FA Cup 1993/94, Fourth Qualifying Round |
| | | Chesham United | – | Kidderminster Harriers | | 1:4 |
| |
FA Cup 1992/93, Fourth Qualifying Round |
| | | Solihull Borough | – | Chesham United | | 3:1 |
| |
FA Cup 1991/92, Fourth Qualifying Round |
| | | Chesham United | – | Aylesbury United | | 1:3 * |
| |
FA Cup 1990/91, Second Qualifying Round |
| | | Chesham United | – | Enfield | | 0:3 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Chesham United | – | Aveley | | 1:2 * |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Hayes | – | Chesham United | | 1:0 |
| |
FA Cup 1987/88, Preliminary Round |
| | | Gorleston | – | Chesham United | | 1:0 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Chesham United | – | Metropolitan Police | | 1:8 |
| |
FA Cup 1985/86, Preliminary Round |
| | | Barton Rovers | – | Chesham United | | 2:1 |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Chesham United | – | Heybridge Swifts | | 1:2 * |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Chesham United | – | Hitchin Town | | 0:2 |
| |
FA Cup 1982/83, First Round Proper |
| 20.11.1982 | | Chesham United | – | Yeovil Town | | 0:1 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Irthlingborough Diamonds | – | Chesham United | | 1:0 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Chesham United | – | St Albans City | | 0:1 |
| |
FA Cup 1979/80, Third Round Proper |
| 05.01.1980 | | Chesham United | – | Cambridge United | | 0:2 |
| |
FA Cup 1978/79, Preliminary Round |
| | | Berkhamsted Town | – | Chesham United | | 1:0 * |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Finchley | – | Chesham United | | 3:2 * |
| |
FA Cup 1976/77, First Round Proper |
| 20.11.1976 | | Brentford | – | Chesham United | | 2:0 |
| Brentford |
FA Cup 1975/76, Third Qualifying Round |
| | | Sutton United | – | Chesham United | | 3:1 |
| |
FA Cup 1974/75, Third Qualifying Round |
| | | Chesham United | – | Wycombe Wanderers | | 1:3 |
| |
FA Cup 1973/74, Second Qualifying Round |
| | | Hertford Town | – | Chesham United | | 2:0 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Chesham United | – | Witney Town | | 0:1 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Carshalton Athletic | – | Chesham United | | 2:1 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Chesham United | – | Cheshunt | | 0:1 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Hitchin Town | – | Chesham United | | 5:0 |
| |
FA Cup 1968/69, First Round Proper |
| 16.11.1968 | | Colchester United | – | Chesham United | | 5:0 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Chesham United | – | Leytonstone | | 0:3 |
| |
FA Cup 1966/67, First Round Proper |
| 26.11.1966 | | Enfield | – | Chesham United | | 6:0 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Banbury United | – | Chesham United | | 2:0 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Hemel Hempstead | – | Chesham United | | 3:2 * |
| |
FA Cup 1963/64, First Qualifying Round |
| | | Oxford City | – | Chesham United | | 5:0 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Hemel Hempstead | – | Chesham United | | 3:0 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Chesham United | – | Banbury Spencer | | 1:4 |
| |
FA Cup 1960/61, Third Qualifying Round |
| | | Chesham United | – | Abingdon Town | | 1:2 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Wokingham Town | – | Chesham United | | 4:1 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Oxford City | – | Chesham United | | 5:2 |
| |
FA Cup 1957/58, Second Qualifying Round |
| | | Marlow | – | Chesham United | | 5:1 * |
| |
FA Cup 1955/56, First Qualifying Round |
| | | Oxford City | – | Chesham United | | 2:1 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Maidenhead United | – | Chesham United | | 5:3 * |
| |
FA Cup 1953/54, Third Qualifying Round |
| | | Headington United | – | Chesham United | | 2:0 |
| |
FA Cup 1952/53, Preliminary Round |
| | | Aylesbury United | – | Chesham United | | 4:1 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Headington United | – | Chesham United | | 5:2 |
| |
FA Cup 1950/51, First Qualifying Round |
| | | Wycombe Wanderers | – | Chesham United | | 4:2 * |
| |
FA Cup 1949/50, Preliminary Round |
| | | Uxbridge | – | Chesham United | | 2:0 |
| |
FA Cup 1948/49, Preliminary Round |
| | | Chesham United | – | Maidenhead United | | 1:4 |
| |
FA Cup 1947/48, Extra Preliminary Round |
| | | Wallingford Town | – | Chesham United | | 4:2 |
| |
FA Cup 1946/47, Preliminary Round |
| | | Uxbridge | – | Chesham United | | 7:2 |
| |
FA Cup 1945/46, Extra Preliminary Round |
| | | Aylesbury United | – | Chesham United | | 5:0 |
| |
