FA Cup 2022/23, Second Qualifying Round |
 | 17.09.2022 |  | Cheshunt | – | St Neots Town | | 3:1 (1:1) |
| Cheshunt |
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, First Qualifying Round |
| 22.09.2020 | | Long Melford | – | Cheshunt | | 1:3 |
| Long Melford |
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, Preliminary Round |
| 25.08.2018 | | Cheshunt | – | Canvey Island | | 1:0 (1:0) |
| 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, Preliminary Round |
| 20.08.2016 | | Cheshunt | – | Basildon United | | 8:0 |
| Cheshunt |
FA Cup 2010/11, Preliminary Round |
| 31.08.2010 | | Cockfosters | – | Cheshunt | | 1:2 * |
| |
FA Cup 2008/09, Preliminary Round |
| 30.08.2008 | | Cheshunt | – | Southend Manor | | 2:1 |
| |
FA Cup 2006/07, Second Qualifying Round |
| 03.10.2006 | | Cheshunt | – | Worthing | | 1:0 * |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Chesham United | – | Cheshunt | | 2:3 |
| |
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 2002/03, First Qualifying Round |
| | | Cheshunt | – | Edgware Town | | 4:0 |
| |
FA Cup 2002/03, Preliminary Round |
| | | Cheshunt | – | Wembley | | 3:0 |
| |
FA Cup 2001/02, Preliminary Round |
| | | Barton Rovers | – | Cheshunt | | 1:3 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Clacton Town | – | Cheshunt | | 2:3 * |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Witham Town | – | Cheshunt | | 0:2 * |
| |
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 1993/94, Preliminary Round |
| | | Cheshunt | – | Clapton | | 2:1 * |
| |
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 1989/90, Preliminary Round |
| | | Wootton Blue Cross | – | Cheshunt | | 0:2 |
| |
FA Cup 1988/89, First Qualifying Round |
| | | Letchworth Garden City | – | Cheshunt | | 1:2 |
| |
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 1975/76, Second Qualifying Round |
| | | Clapton | – | Cheshunt | | 1:2 |
| |
FA Cup 1975/76, First Qualifying Round |
| | | Hemel Hempstead | – | Cheshunt | | 0:2 * |
| |
FA Cup 1970/71, Third Qualifying Round |
| | | Cheshunt | – | Guildford City | | 2:0 * |
| |
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, First Qualifying Round |
| | | Cheshunt | – | Amersham Town | | 3:0 |
| |
FA Cup 1966/67, Third Qualifying Round |
| | | Hertford Town | – | Cheshunt | | 0:1 * |
| |
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 1964/65, First Qualifying Round |
| | | Vauxhall Motors Luton | – | Cheshunt | | 0:2 |
| |
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 1952/53, First Qualifying Round |
| | | Cheshunt | – | Tufnell Park Edmonton | | 2:1 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Cheshunt | – | Ware | | 2:1 |
| |
FA Cup 1950/51, Extra Preliminary Round |
| | | Cheshunt | – | Hoddesdon Town | | 4:2 |
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