FA Cup 2023/24, Fourth Qualifying Round |
 | 17.10.2023 |  | Whitby Town | – | Chelmsford City | | 3:1 (2:0) * |
| Whitby |
FA Cup 2022/23, First Round Proper |
| 14.11.2022 | | Chelmsford City | – | Barnet | | 0:1 (0:0) * |
| Chelmsford |
FA Cup 2021/22, Fourth Qualifying Round |
| 16.10.2021 | | Harrow Borough | – | Chelmsford City | | 4:2 (1:2) |
| London |
FA Cup 2020/21, Second Qualifying Round |
| 03.10.2020 | | Kettering Town | – | Chelmsford City | | 2:0 |
| Kettering |
FA Cup 2019/20, Second Qualifying Round |
| 21.09.2019 | | Corinthian-Casuals | – | Chelmsford City | | 2:0 (1:0) |
| London |
FA Cup 2018/19, Second Qualifying Round |
| 22.09.2018 | | Chelmsford City | – | Worthing | | 1:2 (0:1) |
| Chelmsford |
FA Cup 2017/18, First Round Proper |
| 04.11.2017 | | Gateshead | – | Chelmsford City | | 2:0 (2:0) |
| Gateshead |
FA Cup 2016/17, Second Qualifying Round |
| 17.09.2016 | | Chelmsford City | – | Dartford | | 2:3 |
| Chelmsford |
FA Cup 2015/16, Third Qualifying Round |
| 10.10.2015 | | Basingstoke Town | – | Chelmsford City | | 4:2 (2:1) |
| Basingstoke |
FA Cup 2014/15, Fourth Qualifying Round |
| 28.10.2014 | | Barnet | – | Chelmsford City | | 4:1 (3:0) * |
| London |
FA Cup 2013/14, Second Qualifying Round |
| 28.09.2013 | | Biggleswade Town | – | Chelmsford City | | 2:0 |
| Biggleswade |
FA Cup 2012/13, Second Round Proper |
| 01.12.2012 | | Crawley Town | – | Chelmsford City | | 3:0 (2:0) |
| Crawley |
FA Cup 2011/12, Second Round Proper |
| 14.12.2011 | | Macclesfield Town | – | Chelmsford City | | 1:0 (1:0) * |
| Macclesfield |
FA Cup 2010/11, Second Round Proper |
| 27.11.2010 | | Wycombe Wanderers | – | Chelmsford City | | 3:1 (1:0) |
| High Wycombe |
FA Cup 2009/10, Fourth Qualifying Round |
| 24.10.2009 | | Chelmsford City | – | Stevenage Borough | | 1:2 |
| |
FA Cup 2008/09, Second Qualifying Round |
| 27.09.2008 | | Bury Town | – | Chelmsford City | | 2:1 |
| |
FA Cup 2007/08, Third Qualifying Round |
| 13.10.2007 | | Hayes & Yeading United | – | Chelmsford City | | 1:0 |
| |
FA Cup 2006/07, First Round Proper |
| 21.11.2006 | | Aldershot Town | – | Chelmsford City | | 2:0 (0:0) * |
| Aldershot |
FA Cup 2005/06, Third Qualifying Round |
| 12.10.2005 | | Chelmsford City | – | Nuneaton Borough | | 1:2 * |
| |
FA Cup 2004/05, First Qualifying Round |
| | | Chelmsford City | – | Yeading | | 0:1 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Chelmsford City | – | Eastbourne Borough | | 0:2 * |
| |
FA Cup 2002/03, Third Qualifying Round |
| | | St Albans City | – | Chelmsford City | | 1:0 |
| |
FA Cup 2001/02, Third Qualifying Round |
| | | Harlow Town | – | Chelmsford City | | 3:0 * |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Grays Athletic | – | Chelmsford City | | 2:1 * |
| |
FA Cup 1999/00, First Round Proper |
| 30.10.1999 | | Oldham Athletic | – | Chelmsford City | | 4:0 (2:0) |
| Oldham |
FA Cup 1998/99, Second Qualifying Round |
| | | Chelmsford City | – | Hendon | | 2:3 * |
| |
FA Cup 1997/98, First Qualifying Round |
| | | Yeading | – | Chelmsford City | | 4:2 |
| |
FA Cup 1996/97, Third Qualifying Round |
| | | Chelmsford City | – | Wisbech Town | | 2:3 |
| |
FA Cup 1995/96, Third Qualifying Round |
| | | Billericay Town | – | Chelmsford City | | 2:1 * |
| |
FA Cup 1994/95, First Round Proper |
| 12.11.1994 | | Wycombe Wanderers | – | Chelmsford City | | 4:0 (1:0) |
| |
FA Cup 1993/94, Third Qualifying Round |
| | | Wivenhoe Town | – | Chelmsford City | | 2:0 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Grays Athletic | – | Chelmsford City | | 2:1 * |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Enfield | – | Chelmsford City | | 2:1 * |
| |
FA Cup 1990/91, First Round Proper |
| 21.11.1990 | | Chelmsford City | – | Barnet | | 0:2 * |
| |
FA Cup 1989/90, Fourth Qualifying Round |
| | | Chelmsford City | – | Kidderminster Harriers | | 1:3 * |
| |
FA Cup 1988/89, Fourth Qualifying Round |
| | | Chelmsford City | – | Halesowen Town | | 1:3 |
| |
FA Cup 1987/88, First Round Proper |
| 14.11.1987 | | Chelmsford City | – | Bath City | | 1:2 (1:1) |
| |
FA Cup 1986/87, Second Round Proper |
| 06.12.1986 | | Gillingham | – | Chelmsford City | | 2:0 (1:0) |
| Gillingham |
FA Cup 1985/86, Second Round Proper |
| 07.12.1985 | | Wycombe Wanderers | – | Chelmsford City | | 2:0 |
| |
FA Cup 1984/85, Third Qualifying Round |
| | | Chelmsford City | – | Harlow Town | | 1:2 |
| |
FA Cup 1983/84, Second Round Proper |
| 10.12.1983 | | Gillingham | – | Chelmsford City | | 6:1 |
| |
FA Cup 1982/83, Fourth Qualifying Round |
| | | Chelmsford City | – | Chesham United | | 1:3 |
| |
FA Cup 1981/82, Preliminary Round |
| | | Gorleston | – | Chelmsford City | | 2:0 |
| |
FA Cup 1980/81, Third Qualifying Round |
| | | Wembley | – | Chelmsford City | | 3:1 |
| |
FA Cup 1979/80, First Qualifying Round |
| | | Parson Drove United | – | Chelmsford City | | 2:0 |
| |
FA Cup 1978/79, First Qualifying Round |
| | | Billericay Town | – | Chelmsford City | | 2:1 |
| |
FA Cup 1977/78, Fourth Qualifying Round |
| | | Chelmsford City | – | Folkestone & Shepway | | 0:3 |
| |
FA Cup 1976/77, Fourth Qualifying Round |
| | | Chelmsford City | – | Leatherhead | | 0:4 |
| |
FA Cup 1975/76, Fourth Qualifying Round |
| | | Chelmsford City | – | Bishop's Stortford | | 0:2 |
| |
FA Cup 1974/75, First Round Proper |
| 23.11.1974 | | Chelmsford City | – | Charlton Athletic | | 0:1 |
| |
FA Cup 1973/74, First Round Proper |
| 24.11.1973 | | Watford | – | Chelmsford City | | 1:0 |
| |
FA Cup 1972/73, Third Round Proper |
| 13.01.1973 | | Chelmsford City | – | Ipswich Town | | 1:3 |
| |
FA Cup 1971/72, Fourth Qualifying Round |
| | | Kettering Town | – | Chelmsford City | | 4:1 |
| |
FA Cup 1970/71, Second Round Proper |
| 12.12.1970 | | Chelmsford City | – | Torquay United | | 0:1 |
| |
FA Cup 1969/70, First Round Proper |
| 15.11.1969 | | Chelmsford City | – | Hereford United | | 1:2 (1:1) |
| |
FA Cup 1968/69, First Round Proper |
| 16.11.1968 | | Grantham | – | Chelmsford City | | 2:1 |
| |
FA Cup 1967/68, Second Round Proper |
| 06.01.1968 | | Chelmsford City | – | Colchester United | | 0:2 |
| |
FA Cup 1966/67, First Round Proper |
| 26.11.1966 | | Brentford | – | Chelmsford City | | 1:0 |
| |
FA Cup 1965/66, Fourth Qualifying Round |
| | | Romford | – | Chelmsford City | | 2:1 |
| |
FA Cup 1964/65, First Round Proper |
| 14.11.1964 | | Notts County | – | Chelmsford City | | 2:0 |
| |
FA Cup 1963/64, Second Round Proper |
| 07.12.1963 | | Chelmsford City | – | Bedford Town | | 0:1 |
| |
FA Cup 1962/63, First Round Proper |
| 03.11.1962 | | Chelmsford City | – | Shrewsbury Town | | 2:6 |
| |
FA Cup 1961/62, First Round Proper |
| 04.11.1961 | | Chelmsford City | – | King's Lynn | | 1:2 |
| |
FA Cup 1960/61, First Round Proper |
| 05.11.1960 | | Chelmsford City | – | Port Vale | | 2:3 |
| |
FA Cup 1959/60, First Round Proper |
| 14.11.1959 | | Crystal Palace | – | Chelmsford City | | 5:1 |
| |
FA Cup 1958/59, First Round Proper |
| 21.11.1958 | | Worcester City | – | Chelmsford City | | 3:1 * |
| |
FA Cup 1957/58, Fourth Qualifying Round |
| | | Gorleston | – | Chelmsford City | | 1:0 |
| |
FA Cup 1956/57, Third Qualifying Round |
| | | Chelmsford City | – | Clacton Town | | 1:2 * |
| |
FA Cup 1955/56, Preliminary Round |
| | | Grays Athletic | – | Chelmsford City | | 1:0 |
| |
FA Cup 1954/55, First Round Proper |
| 20.11.1954 | | Aldershot | – | Chelmsford City | | 3:1 |
| |
FA Cup 1953/54, Fourth Qualifying Round |
| | | Great Yarmouth Town | – | Chelmsford City | | 1:0 * |
| |
FA Cup 1952/53, Fourth Qualifying Round |
| | | Finchley | – | Chelmsford City | | 3:0 * |
| |
FA Cup 1951/52, Fourth Qualifying Round |
| | | Leytonstone | – | Chelmsford City | | 2:1 |
| |
FA Cup 1950/51, Second Round Proper |
| 09.12.1950 | | Chelmsford City | – | Mansfield Town | | 1:4 |
| |
FA Cup 1949/50, Second Round Proper |
| 15.12.1949 | | Ipswich Town | – | Chelmsford City | | 1:0 * |
| |
FA Cup 1948/49, First Round Proper |
| 27.11.1948 | | Weymouth | – | Chelmsford City | | 2:1 |
| |
FA Cup 1947/48, Fourth Qualifying Round |
| | | Colchester United | – | Chelmsford City | | 3:1 |
| |
FA Cup 1946/47, Fourth Qualifying Round |
| | | Chelmsford City | – | Cambridge Town | | 0:4 |
| |
FA Cup 1945/46, First Round Proper |
| 24.11.1945 | | Chelmsford City | – | Northampton Town | | 0:5 |
| |
FA Cup 1945/46, First Round Proper |
| 17.11.1945 | | Northampton Town | – | Chelmsford City | | 5:1 |
| |
FA Cup 1938/39, Fourth Round Proper |
| 21.01.1939 | | Birmingham | – | Chelmsford City | | 6:0 |
| |
FA Cup 1931/32, First Round Proper |
| 28.11.1931 | | Aldershot | – | Chelmsford | | 7:0 |
| |
