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 2021/22, Third qualifying round |
| 02.10.2021 | | AFC Sudbury | – | Cheshunt | | 1:0 (1:0) |
| Sudbury |
FA Cup 2020/21, Second Qualifying Round |
| 03.10.2020 | | Cheshunt | – | Cambridge City | | 1:2 |
| Cheshunt |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Maidstone United | – | Cheshunt | | 4:1 (2:0) |
| Maidstone |
FA Cup 2018/19, First Qualifying Round |
| 11.09.2018 | | Leiston | – | Cheshunt | | 4:2 (2:0) * |
| Leiston |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Cheshunt | – | Dorking Wanderers | | 1:3 (1:2) |
| Cheshunt |
FA Cup 2016/17, First Qualifying Round |
| 03.09.2016 | | Hendon | – | Cheshunt | | 5:2 |
| London Hendon cricket ground |
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 2011/12, Preliminary Round |
| 06.09.2011 | | Southend Manor | – | Cheshunt | | 4:2 * |
| |
FA Cup 2010/11, First Qualifying Round |
| 12.09.2010 | | Hendon | – | Cheshunt | | 4:1 |
| |
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 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 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 2003/04, Preliminary Round |
| | | Cheshunt | – | Harlow Town | | 2:3 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Lymington & New Milton | – | Cheshunt | | 3:1 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Arlesey Town | – | Cheshunt | | 2:0 |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Hemel Hempstead Town | – | Cheshunt | | 3:0 |
| |
FA Cup 1999/00, Third Qualifying Round |
| | | Baldock Town | – | Cheshunt | | 5:1 |
| |
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, First Qualifying Round |
| | | Cheshunt | – | Burnham | | 0:2 |
| |
FA Cup 1992/93, Second Qualifying Round |
| | | Solihull Borough | – | Cheshunt | | 4:0 * |
| |
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 1988/89, Second Qualifying Round |
| | | Cheshunt | – | Staines Town | | 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 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 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 1976/77, First Qualifying Round |
| | | Windsor & Eton | – | Cheshunt | | 3:2 |
| |
FA Cup 1975/76, Third Qualifying Round |
| | | Romford | – | Cheshunt | | 1:0 |
| |
FA Cup 1974/75, Preliminary Round |
| | | Edmonton & Haringey | – | Cheshunt | | 2:1 |
| |
FA Cup 1973/74, First Qualifying Round |
| | | Dagenham | – | Cheshunt | | 2:1 * |
| |
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 1969/70, Second Qualifying Round |
| | | Hitchin Town | – | Cheshunt | | 3:1 |
| |
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 1966/67, Fourth Qualifying Round |
| | | Wycombe Wanderers | – | Cheshunt | | 8:0 |
| |
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 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 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 1951/52, First Qualifying Round |
| | | Cheshunt | – | Leyton | | 1:2 |
| |
FA Cup 1950/51, First Qualifying Round |
| | | Hayes | – | Cheshunt | | 7:1 |
| |
