FA Cup 2023/24, Extra Preliminary Round |
 | 04.08.2023 | | Woodford Town | – | Hertford Town | | 4:1 (3:0) |
| London Ashton Playing Fields |
FA Cup 2022/23, First Qualifying Round |
| 03.09.2022 | | Hertford Town | – | Royston Town | | 0:3 (0:2) |
| Hertford |
FA Cup 2021/22, Preliminary Round |
| 24.08.2021 | | Hertford Town | – | Little Oakley | | 1:2 (1:0) * |
| Hertford |
FA Cup 2020/21, Preliminary Round |
| 12.09.2020 | | Hertford Town | – | Maldon & Tiptree | | 0:1 |
| Hertford |
FA Cup 2019/20, Preliminary Round |
| 24.08.2019 | | Whitton United | – | Hertford Town | | 2:1 (0:0) |
| Ipswich |
FA Cup 2018/19, First Qualifying Round |
| 08.09.2018 | | Corby Town | – | Hertford Town | | 2:0 (1:0) |
| Corby |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Hertford Town | – | AFC Hornchurch | | 1:2 (1:0) |
| Hertford |
FA Cup 2016/17, Preliminary Round |
| 20.08.2016 | | Hertford Town | – | Hadley | | 0:1 |
| Hertford |
FA Cup 2015/16, Extra Preliminary Round |
| 18.08.2015 | | Kirkley & Pakefield | – | Hertford Town | | 2:1 * |
| Lowestoft |
FA Cup 2014/15, First Qualifying Round |
| 13.09.2014 | | Hertford Town | – | Canvey Island | | 1:4 (0:1) |
| Hertford |
FA Cup 2013/14, First Qualifying Round |
| 14.09.2013 | | Hertford Town | – | Dunstable Town | | 0:6 |
| Hertford |
FA Cup 2012/13, Extra Preliminary Round |
| 11.08.2012 | | Hadley | – | Hertford Town | | 2:0 |
| |
FA Cup 2011/12, First Qualifying Round |
| 17.09.2011 | | Hertford Town | – | Oxhey Jets | | 0:1 |
| |
FA Cup 2010/11, Preliminary Round |
| 28.08.2010 | | Maldon & Tiptree | – | Hertford Town | | 4:2 |
| |
FA Cup 2009/10, Extra Preliminary Round |
| 14.08.2009 | | Hertford Town | – | Newport Pagnell Town | | 1:2 |
| |
FA Cup 2008/09, Extra Preliminary Round |
| 16.08.2008 | | Oxhey Jets | – | Hertford Town | | 5:0 |
| |
FA Cup 2007/08, First Qualifying Round |
| 17.09.2007 | | Barkingside | – | Hertford Town | | 3:1 * |
| |
FA Cup 2006/07, Extra Preliminary Round |
| 19.08.2006 | | Hertford Town | – | Stotfold | | 1:2 |
| |
FA Cup 2005/06, Preliminary Round |
| 27.08.2005 | | Hertford Town | – | Ruislip Manor | | 1:2 |
| |
FA Cup 2004/05, Second Qualifying Round |
| | | Ashford Town Middlesex | – | Hertford Town | | 3:1 |
| |
FA Cup 2003/04, Preliminary Round |
| | | Hertford Town | – | Lowestoft Town | | 2:4 |
| |
FA Cup 2002/03, First Qualifying Round |
| | | Hertford Town | – | AFC Wallingford | | 1:4 |
| |
FA Cup 2001/02, First Qualifying Round |
| | | Hertford Town | – | St Margaretsbury | | 0:4 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Hertford Town | – | Ford Sports Daventry | | 2:3 * |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Hertford Town | – | Royston Town | | 0:2 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Barkingside | – | Hertford Town | | 3:2 * |
| |
FA Cup 1997/98, Preliminary Round |
| | | Romford | – | Hertford Town | | 2:0 |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Hertford Town | – | Potters Bar Town | | 1:2 |
| |
FA Cup 1995/96, Third Qualifying Round |
| | | Hertford Town | – | Sudbury Wanderers | | 0:2 |
| |
FA Cup 1994/95, Preliminary Round |
| | | Hertford Town | – | Saffron Walden Town | | 2:5 |
| |
FA Cup 1993/94, Preliminary Round |
| | | Hertford Town | – | Kempston Rovers | | 0:1 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Hertford Town | – | Hendon | | 0:2 |
| |
FA Cup 1991/92, Third Qualifying Round |
| | | Hertford Town | – | Windsor & Eton | | 1:2 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Hertford Town | – | Chesham United | | 1:5 * |
| |
FA Cup 1989/90, First Qualifying Round |
| | | Hertford Town | – | Burnham | | 0:1 |
| |
FA Cup 1988/89, Second Qualifying Round |
| | | Wokingham Town | – | Hertford Town | | 3:1 |
| |
FA Cup 1987/88, Third Qualifying Round |
| | | Hertford Town | – | Aylesbury United | | 0:4 |
| |
FA Cup 1986/87, First Qualifying Round |
| | | Woodford Town | – | Hertford Town | | 2:0 |
| |
FA Cup 1985/86, Preliminary Round |
| | | Harefield United | – | Hertford Town | | 3:0 * |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Sutton Coldfield Town | – | Hertford Town | | 2:1 * |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Bognor Regis Town | – | Hertford Town | | 2:0 * |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Wealdstone | – | Hertford Town | | 5:0 |
| |
FA Cup 1981/82, Third Qualifying Round |
| | | Corinthian-Casuals | – | Hertford Town | | 2:0 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Kempston Rovers | – | Hertford Town | | 3:0 |
| |
FA Cup 1979/80, Second Qualifying Round |
| | | Hertford Town | – | Bedford Town | | 0:2 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Sutton United | – | Hertford Town | | 2:1 |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Hertford Town | – | Letchworth Garden City | | 0:3 |
| |
FA Cup 1976/77, First Qualifying Round |
| | | Hertford Town | – | Boreham Wood | | 1:2 |
| |
FA Cup 1975/76, Preliminary Round |
| | | Hertford Town | – | Burnham | | 0:2 |
| |
FA Cup 1974/75, First Qualifying Round |
| | | Dunstable Town | – | Hertford Town | | 3:2 |
| |
FA Cup 1973/74, Fourth Qualifying Round |
| | | Hillingdon Borough | – | Hertford Town | | 2:1 |
| |
FA Cup 1972/73, Second Qualifying Round |
| | | Barking | – | Hertford Town | | 1:0 |
| |
FA Cup 1971/72, Preliminary Round |
| | | Leytonstone | – | Hertford Town | | 2:1 * |
| |
FA Cup 1970/71, First Qualifying Round |
| | | Hertford Town | – | Bexley United | | 1:2 * |
| |
FA Cup 1969/70, Third Qualifying Round |
| | | Hertford Town | – | Hendon | | 2:4 |
| |
FA Cup 1968/69, First Qualifying Round |
| | | Hendon | – | Hertford Town | | 1:0 * |
| |
FA Cup 1967/68, Second Qualifying Round |
| | | Slough Town | – | Hertford Town | | 3:0 |
| |
FA Cup 1966/67, Third Qualifying Round |
| | | Hertford Town | – | Cheshunt | | 0:1 * |
| |
FA Cup 1965/66, First Qualifying Round |
| | | Hertford Town | – | Wealdstone | | 1:2 |
| |
FA Cup 1964/65, Second Qualifying Round |
| | | Hertford Town | – | Barnet | | 0:2 * |
| |
FA Cup 1963/64, Second Qualifying Round |
| | | Barnet | – | Hertford Town | | 3:1 |
| |
FA Cup 1962/63, First Qualifying Round |
| | | Barnet | – | Hertford Town | | 2:0 |
| |
FA Cup 1961/62, First Qualifying Round |
| | | Enfield | – | Hertford Town | | 8:1 |
| |
FA Cup 1960/61, Second Qualifying Round |
| | | Harrow Town | – | Hertford Town | | 3:2 |
| |
FA Cup 1959/60, Third Qualifying Round |
| | | Hertford Town | – | Enfield | | 2:3 |
| |
FA Cup 1958/59, First Qualifying Round |
| | | Hertford Town | – | Enfield | | 0:2 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Eton Manor | – | Hertford Town | | 3:1 |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Hertford Town | – | Hitchin Town | | 0:1 |
| |
FA Cup 1955/56, Preliminary Round |
| | | Hertford Town | – | St Albans City | | 1:2 |
| |
FA Cup 1950/51, Preliminary Round |
| | | Hertford Town | – | Wealdstone | | 1:3 |
| |
FA Cup 1949/50, Extra Preliminary Round |
| | | Hertford Town | – | Finchley | | 3:5 |
| |
FA Cup 1946/47, First Qualifying Round |
| | | St Albans City | – | Hertford Town | | 5:1 |
| |
FA Cup 1945/46, Preliminary Round |
| | | Hertford Town | – | Enfield | | 3:6 |
| |
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