FA Cup 2023/24, First Qualifying Round |
 | 02.09.2023 | | Royston Town | – | Cheshunt | | 1:0 (0:0) |
| Royston |
FA Cup 2022/23, Third Qualifying Round |
| 01.10.2022 | | Cheshunt | – | Kidderminster Harriers | | 1:2 (0:1) |
| Cheshunt |
FA Cup 2022/23, Second Qualifying Round |
| 17.09.2022 | | Cheshunt | – | St Neots Town | | 3:1 (1:1) |
| Cheshunt |
FA Cup 2021/22, Third qualifying round |
| 02.10.2021 | | AFC Sudbury | – | Cheshunt | | 1:0 (1:0) |
| Sudbury |
FA Cup 2021/22, Second qualifying round |
| 18.09.2021 | | Hitchin Town | – | Cheshunt | | 0:3 (0:0) |
| Hitchin |
FA Cup 2021/22, First Qualifying Round |
| 04.09.2021 | | Brentwood Town | – | Cheshunt | | 0:2 (0:0) |
| Brentwood |
FA Cup 2020/21, Second Qualifying Round |
| 03.10.2020 | | Cheshunt | – | Cambridge City | | 1:2 |
| Cheshunt |
FA Cup 2020/21, First Qualifying Round |
| 22.09.2020 | | Long Melford | – | Cheshunt | | 1:3 |
| Long Melford |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Maidstone United | – | Cheshunt | | 4:1 (2:0) |
| Maidstone |
FA Cup 2019/20, First Qualifying Round |
| 07.09.2019 | | Cheshunt | – | Brightlingsea Regent | | 1:0 (0:0) |
| Cheshunt |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Cheshunt | – | Stowmarket Town | | 1:0 (0:0) |
| Cheshunt |
FA Cup 2018/19, First Qualifying Round |
| 11.09.2018 | | Leiston | – | Cheshunt | | 4:2 (2:0) * |
| Leiston |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Cheshunt | – | Leiston | | 2:2 (1:0) |
| Cheshunt |
FA Cup 2018/19, Preliminary Round |
| 25.08.2018 | | Cheshunt | – | Canvey Island | | 1:0 (1:0) |
| Cheshunt |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Cheshunt | – | Dorking Wanderers | | 1:3 (1:2) |
| Cheshunt |
FA Cup 2017/18, First Qualifying Round |
| 02.09.2017 | | Cheshunt | – | Takeley | | 2:0 (0:0) |
| Cheshunt |
FA Cup 2017/18, Preliminary Round |
| 19.08.2017 | | Brantham Athletic | – | Cheshunt | | 3:5 (1:1) |
| Brantham |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Hendon | – | Cheshunt | | 5:2 |
| London Hendon cricket ground |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | Cheshunt | – | Basildon United | | 8:0 |
| Cheshunt |
FA Cup 2015/16, Preliminary Round |
| 29.08.2015 | | Saffron Walden Town | – | Cheshunt | | 2:0 |
| Saffron Walden |
FA Cup 2014/15, Preliminary Round |
| 30.08.2014 | | Cheshunt | – | Thurrock | | 0:1 |
| Cheshunt |
FA Cup 2013/14, Preliminary Round |
| 31.08.2013 | | Hertford Town | – | Cheshunt | | 4:2 |
| Hertford |
FA Cup 2012/13, Preliminary Round |
| 28.08.2012 | | Potters Bar Town | – | Cheshunt | | 3:1 * |
| Potters Bar |
FA Cup 2012/13, Preliminary Round |
| 25.08.2012 | | Cheshunt | – | Potters Bar Town | | 2:2 |
| Cheshunt |
FA Cup 2011/12, Preliminary Round |
| 06.09.2011 | | Southend Manor | – | Cheshunt | | 4:2 * |
| |
FA Cup 2011/12, Preliminary Round |
| 03.09.2011 | | Cheshunt | – | Southend Manor | | 0:0 |
| |
FA Cup 2010/11, First Qualifying Round |
| 12.09.2010 | | Hendon | – | Cheshunt | | 4:1 |
| |
FA Cup 2010/11, Preliminary Round |
| 31.08.2010 | | Cockfosters | – | Cheshunt | | 1:2 * |
| |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Cheshunt | – | Cockfosters | | 2:2 |
| |
FA Cup 2009/10, Preliminary Round |
| 29.08.2009 | | Cheshunt | – | Maldon Town | | 2:3 |
| |
FA Cup 2008/09, First Qualifying Round |
| 13.09.2008 | | Cheshunt | – | Staines Town | | 0:3 |
| |
FA Cup 2008/09, Preliminary Round |
| 30.08.2008 | | Cheshunt | – | Southend Manor | | 2:1 |
| |
FA Cup 2007/08, First Qualifying Round |
| 15.09.2007 | | AFC Hornchurch | – | Cheshunt | | 3:1 |
| |
FA Cup 2006/07, Third Qualifying Round |
| 14.10.2006 | | Cheshunt | – | Tonbridge Angels | | 1:2 |
| |
FA Cup 2006/07, Second Qualifying Round |
| 03.10.2006 | | Cheshunt | – | Worthing | | 1:0 * |
| |
FA Cup 2006/07, Second Qualifying Round |
| 30.09.2006 | | Worthing | – | Cheshunt | | 0:0 |
| |
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 | | Cheshunt | – | Braintree Town | | 1:2 |
| |
FA Cup 2004/05, Third Qualifying Round |
| | | Slough Town | – | Cheshunt | | 4:0 (0:0) |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Cheshunt | – | Northwood | | 3:0 |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Barton Rovers | – | Cheshunt | | 3:4 * |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Cheshunt | – | Barton Rovers | | 2:2 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Cheshunt | – | Harlow Town | | 2:3 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Lymington & New Milton | – | Cheshunt | | 3:1 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Cheshunt | – | Edgware Town | | 4:0 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Cheshunt | – | Wembley | | 3:0 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Arlesey Town | – | Cheshunt | | 2:0 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Barton Rovers | – | Cheshunt | | 1:3 |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Hemel Hempstead Town | – | Cheshunt | | 3:0 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Clacton Town | – | Cheshunt | | 2:3 * |
| |
FA Cup 2000/01, Preliminary Round |
| | | Cheshunt | – | Clacton Town | | 2:2 |
| |
FA Cup 1999/00, Third Qualifying Round |
| | | Baldock Town | – | Cheshunt | | 5:1 |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Witham Town | – | Cheshunt | | 0:2 * |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Cheshunt | – | Witham Town | | 0:0 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Cheshunt | – | Waltham Abbey | | 1:0 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Wootton Blue Cross | – | Cheshunt | | 0:2 |
| |
FA Cup 1998/99, Preliminary Round |
| | | Desborough Town | – | Cheshunt | | 1:0 |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Cheshunt | – | Sutton United | | 0:4 |
| |
FA Cup 1996/97, Preliminary Round |
| | | Potters Bar Town | – | Cheshunt | | 5:1 |
| |
FA Cup 1995/96, Preliminary Round |
| | | Cheshunt | – | Wealdstone | | 0:1 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Collier Row | – | Cheshunt | | 2:1 |
| |
FA Cup 1993/94, Preliminary Round |
| | | Cheshunt | – | Clapton | | 2:1 * |
| |
FA Cup 1993/94, Preliminary Round |
| | | Clapton | – | Cheshunt | | 1:1 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Cheshunt | – | Burnham | | 0:2 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Solihull Borough | – | Cheshunt | | 4:0 * |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Cheshunt | – | Solihull Borough | | 0:0 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Cheshunt | – | Chalfont St Peter | | 1:0 |
| |
FA Cup 1992/93, Preliminary Round |
| | | Spalding United | – | Cheshunt | | 0:5 * |
| |
FA Cup 1992/93, Preliminary Round |
| | | Cheshunt | – | Spalding United | | 0:0 |
| |
FA Cup 1991/92, Preliminary Round |
| | | Cheshunt | – | Tilbury | | 0:3 |
| |
FA Cup 1990/91, Preliminary Round |
| | | Newmarket Town | – | Cheshunt | | 2:1 |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Ware | – | Cheshunt | | 2:0 |
| |
FA Cup 1989/90, Preliminary Round |
| | | Wootton Blue Cross | – | Cheshunt | | 0:2 |
| |
FA Cup 1988/89, Second Qualifying Round |
| | | Cheshunt | – | Staines Town | | 1:2 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Letchworth Garden City | – | Cheshunt | | 1:2 |
| |
FA Cup 1986/87, Preliminary Round |
| | | Cheshunt | – | Rainham Town | | 1:2 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Barking | – | Cheshunt | | 4:1 |
| |
FA Cup 1984/85, Preliminary Round |
| | | Cheshunt | – | Arlesey Town | | 0:1 * |
| |
FA Cup 1984/85, Preliminary Round |
| | | Arlesey Town | – | Cheshunt | | 2:2 |
| |
FA Cup 1983/84, Preliminary Round |
| | | Stowmarket | – | Cheshunt | | 1:0 |
| |
FA Cup 1982/83, Preliminary Round |
| | | Barton Rovers | – | Cheshunt | | 2:0 |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Cheshunt | – | Lewes | | 0:2 * |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Lewes | – | Cheshunt | | 3:3 aet * |
| |
FA Cup 1981/82, First Qualifying Round |
| | | Cheshunt | – | Lewes | | 2:2 |
| |
FA Cup 1980/81, Preliminary Round |
| | | Cheshunt | – | Clapton | | 0:1 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Cheshunt | – | Barking | | 1:5 |
| |
FA Cup 1978/79, Preliminary Round |
| | | Grays Athletic | – | Cheshunt | | 5:1 |
| |
FA Cup 1977/78, Fourth Qualifying Round |
| | | Leatherhead | – | Cheshunt | | 4:1 |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Cheshunt | – | Hillingdon Borough | | 1:0 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Cheshunt | – | Clapton | | 2:1 |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Cheshunt | – | Walton & Hersham | | 3:2 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Windsor & Eton | – | Cheshunt | | 3:2 |
| |
FA Cup 1975/76, Third Qualifying Round |
| | | Romford | – | Cheshunt | | 1:0 |
| |
FA Cup 1975/76, Second Qualifying Round |
| | | Clapton | – | Cheshunt | | 1:2 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Hemel Hempstead | – | Cheshunt | | 0:2 * |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Cheshunt | – | Hemel Hempstead | | 2:2 |
| |
FA Cup 1974/75, Preliminary Round |
| | | Edmonton & Haringey | – | Cheshunt | | 2:1 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Dagenham | – | Cheshunt | | 2:1 * |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Cheshunt | – | Dagenham | | 0:0 aet * |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Dagenham | – | Cheshunt | | 2:2 aet * |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Cheshunt | – | Dagenham | | 2:2 |
| |
FA Cup 1972/73, First Qualifying Round |
| | | Cheshunt | – | Wimbledon | | 0:4 |
| |
FA Cup 1971/72, First Qualifying Round |
| | | Boreham Wood | – | Cheshunt | | 2:1 |
| |
FA Cup 1970/71, Fourth Qualifying Round |
| | | Bishop's Stortford | – | Cheshunt | | 5:2 |
| |
FA Cup 1970/71, Third Qualifying Round |
| | | Cheshunt | – | Guildford City | | 2:0 * |
| |
FA Cup 1970/71, Third Qualifying Round |
| | | Guildford City | – | Cheshunt | | 1:1 |
| |
FA Cup 1970/71, Second Qualifying Round |
| | | Cheshunt | – | Stevenage Athletic | | 3:1 |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Chesham United | – | Cheshunt | | 0:1 |
| |
FA Cup 1969/70, Second Qualifying Round |
| | | Hitchin Town | – | Cheshunt | | 3:1 |
| |
FA Cup 1969/70, First Qualifying Round |
| | | Cheshunt | – | Amersham Town | | 3:0 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Hitchin Town | – | Cheshunt | | 3:1 |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Erith & Belvedere | – | Cheshunt | | 4:3 * |
| |
FA Cup 1967/68, First Qualifying Round |
| | | Cheshunt | – | Erith & Belvedere | | 4:4 |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Wycombe Wanderers | – | Cheshunt | | 8:0 |
| |
FA Cup 1966/67, Third Qualifying Round |
| | | Hertford Town | – | Cheshunt | | 0:1 * |
| |
FA Cup 1966/67, Third Qualifying Round |
| | | Cheshunt | – | Hertford Town | | 0:0 |
| |
FA Cup 1966/67, Second Qualifying Round |
| | | Cheshunt | – | Rainham Town | | 5:2 |
| |
FA Cup 1966/67, First Qualifying Round |
| | | Ford United | – | Cheshunt | | 0:1 |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Ware | – | Cheshunt | | 3:1 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Bletchley Town | – | Cheshunt | | 1:0 * |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Cheshunt | – | Bletchley Town | | 1:1 |
| |
FA Cup 1964/65, First Qualifying Round |
| | | Vauxhall Motors Luton | – | Cheshunt | | 0:2 |
| |
FA Cup 1960/61, First Qualifying Round |
| | | Cheshunt | – | Bishop's Stortford | | 0:2 |
| |
FA Cup 1959/60, First Qualifying Round |
| | | Hertford Town | – | Cheshunt | | 7:0 |
| |
FA Cup 1958/59, Fourth Qualifying Round |
| | | Cheshunt | – | King's Lynn | | 0:6 |
| |
FA Cup 1958/59, Third Qualifying Round |
| | | Cheshunt | – | Enfield | | 3:1 |
| |
FA Cup 1958/59, Second Qualifying Round |
| | | St Albans City | – | Cheshunt | | 2:3 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Cheshunt | – | Hoddesdon Town | | 4:0 |
| |
FA Cup 1958/59, Preliminary Round |
| | | Cheshunt | – | Bishop's Stortford | | 3:2 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Enfield | – | Cheshunt | | 3:0 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Stevenage Town | – | Cheshunt | | 6:1 |
| |
FA Cup 1952/53, Second Qualifying Round |
| | | Cheshunt | – | Eton Manor | | 0:1 |
| |
FA Cup 1952/53, First Qualifying Round |
| | | Cheshunt | – | Tufnell Park Edmonton | | 2:1 |
| |
FA Cup 1951/52, First Qualifying Round |
| | | Cheshunt | – | Leyton | | 1:2 |
| |
FA Cup 1950/51, First Qualifying Round |
| | | Hayes | – | Cheshunt | | 7:1 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Cheshunt | – | Ware | | 2:1 |
| |
FA Cup 1950/51, Extra Preliminary Round |
| | | Cheshunt | – | Hoddesdon Town | | 4:2 |
| |
