FA Cup 2023/24, Fourth Qualifying Round |
 | 14.10.2023 |  | Chelmsford City | – | Whitby Town | | 2:2 (0:1) |
| Chelmsford |
FA Cup 2023/24, Third Qualifying Round |
| 30.09.2023 | | Bromsgrove Sporting | – | Chelmsford City | | 2:2 (0:0) |
| Bromsgrove |
FA Cup 2023/24, Second Qualifying Round |
| 16.09.2023 | | Ware | – | Chelmsford City | | 3:3 (1:2) |
| Ware |
FA Cup 2022/23, First Round Proper |
| 05.11.2022 | | Barnet | – | Chelmsford City | | 1:1 (0:0) |
| London |
FA Cup 2017/18, Fourth Qualifying Round |
| 14.10.2017 | | Bath City | – | Chelmsford City | | 0:0 |
| Bath |
FA Cup 2015/16, Second Qualifying Round |
| 26.09.2015 | | Chelmsford City | – | Ebbsfleet United | | 0:0 |
| Chelmsford |
FA Cup 2014/15, Fourth Qualifying Round |
| 25.10.2014 | | Chelmsford City | – | Barnet | | 0:0 |
| Chelmsford Chelmsford Sports and Athletics Stadium |
FA Cup 2014/15, Third Qualifying Round |
| 11.10.2014 | | Whitehawk | – | Chelmsford City | | 4:4 (3:3) |
| Whitehawk |
FA Cup 2012/13, Fourth Qualifying Round |
| 23.10.2012 | | East Thurrock United | – | Chelmsford City | | 4:4 aet
(1:1, 2:2),
pen. 3:5 * |
| Corringham |
FA Cup 2012/13, Fourth Qualifying Round |
| 20.10.2012 | | Chelmsford City | – | East Thurrock United | | 2:2 (1:1) |
| Chelmsford |
FA Cup 2011/12, Second Round Proper |
| 03.12.2011 | | Chelmsford City | – | Macclesfield Town | | 1:1 (1:0) |
| Chelmsford |
FA Cup 2011/12, Fourth Qualifying Round |
| 29.10.2011 | | Chelmsford City | – | Gloucester City | | 1:1 (0:1) |
| Chelmsford |
FA Cup 2010/11, Fourth Qualifying Round |
| 23.10.2010 | | Carshalton Athletic | – | Chelmsford City | | 1:1 |
| |
FA Cup 2010/11, Third Qualifying Round |
| 09.10.2010 | | Chelmsford City | – | Bromley | | 2:2 |
| |
FA Cup 2006/07, First Round Proper |
| 11.11.2006 | | Chelmsford City | – | Aldershot Town | | 1:1 (0:0) |
| Chelmsford |
FA Cup 2006/07, Second Qualifying Round |
| 30.09.2006 | | Dereham Town | – | Chelmsford City | | 2:2 |
| |
FA Cup 2005/06, Third Qualifying Round |
| 08.10.2005 | | Nuneaton Borough | – | Chelmsford City | | 1:1 |
| |
FA Cup 2005/06, First Qualifying Round |
| 10.09.2005 | | Chelmsford City | – | Harlow Town | | 1:1 |
| |
FA Cup 2003/04, Second Qualifying Round |
| | | Eastbourne Borough | – | Chelmsford City | | 2:2 |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Carshalton Athletic | – | Chelmsford City | | 1:1 |
| |
FA Cup 2001/02, Third Qualifying Round |
| | | Chelmsford City | – | Harlow Town | | 1:1 |
| |
FA Cup 2000/01, Second Qualifying Round |
| | | Chelmsford City | – | Grays Athletic | | 1:1 |
| |
FA Cup 1998/99, Second Qualifying Round |
| | | Hendon | – | Chelmsford City | | 1:1 |
| |
FA Cup 1996/97, Second Qualifying Round |
| | | Heybridge Swifts | – | Chelmsford City | | 1:1 |
| |
FA Cup 1995/96, Third Qualifying Round |
| | | Chelmsford City | – | Billericay Town | | 1:1 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Holbeach United | – | Chelmsford City | | 0:0 |
| |
FA Cup 1994/95, Fourth Qualifying Round |
| | | Valley Sports Rugby | – | Chelmsford City | | 0:0 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Newmarket Town | – | Chelmsford City | | 1:1 * |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Chelmsford City | – | Newmarket Town | | 0:0 |
| |
FA Cup 1992/93, First Qualifying Round |
| | | Chelmsford City | – | Grays Athletic | | 0:0 |
| |
FA Cup 1991/92, Second Qualifying Round |
| | | Chelmsford City | – | Enfield | | 1:1 |
| |
FA Cup 1990/91, First Round Proper |
| 17.11.1990 | | Barnet | – | Chelmsford City | | 2:2 |
| London |
FA Cup 1990/91, Fourth Qualifying Round |
| | | Chelmsford City | – | Kettering Town | | 0:0 |
| |
FA Cup 1990/91, Third Qualifying Round |
| | | Enfield | – | Chelmsford City | | 1:1 |
| |
FA Cup 1989/90, Fourth Qualifying Round |
| | | Kidderminster Harriers | – | Chelmsford City | | 2:2 |
| |
FA Cup 1986/87, First Round Proper |
| 15.11.1986 | | Woking | – | Chelmsford City | | 1:1 (0:0) |
| Woking |
FA Cup 1984/85, Second Qualifying Round |
| | | Hornchurch | – | Chelmsford City | | 1:1 |
| |
FA Cup 1983/84, First Round Proper |
| 19.11.1983 | | Chelmsford City | – | Wycombe Wanderers | | 0:0 |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Chelmsford City | – | Valley Sports Rugby | | 2:2 |
| |
FA Cup 1982/83, Third Qualifying Round |
| | | Leytonstone/Ilford | – | Chelmsford City | | 0:0 aet * |
| |
FA Cup 1982/83, Third Qualifying Round |
| | | Chelmsford City | – | Leytonstone/Ilford | | 0:0 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Sudbury Town | – | Chelmsford City | | 1:1 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Chelmsford City | – | Clacton Town | | 0:0 |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Harlow Town | – | Chelmsford City | | 1:1 |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Gorleston | – | Chelmsford City | | 1:1 |
| |
FA Cup 1970/71, First Round Proper |
| 21.11.1970 | | Crawley Town | – | Chelmsford City | | 1:1 |
| |
FA Cup 1968/69, Fourth Qualifying Round |
| | | Kingstonian | – | Chelmsford City | | 3:3 |
| |
FA Cup 1967/68, First Round Proper |
| 13.12.1967 | | Oxford United | – | Chelmsford City | | 3:3 aet * |
| |
FA Cup 1967/68, First Round Proper |
| 09.12.1967 | | Chelmsford City | – | Oxford United | | 3:3 |
| |
FA Cup 1961/62, Fourth Qualifying Round |
| | | Wisbech Town | – | Chelmsford City | | 3:3 |
| |
FA Cup 1960/61, Fourth Qualifying Round |
| | | Chelmsford City | – | Wisbech Town | | 3:3 |
| |
FA Cup 1958/59, First Round Proper |
| 15.11.1958 | | Chelmsford City | – | Worcester City | | 0:0 |
| |
FA Cup 1956/57, Third Qualifying Round |
| | | Clacton Town | – | Chelmsford City | | 0:0 aet * |
| |
FA Cup 1956/57, Third Qualifying Round |
| | | Chelmsford City | – | Clacton Town | | 2:2 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Barking | – | Chelmsford City | | 1:1 aet * |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Chelmsford City | – | Barking | | 2:2 |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Leytonstone | – | Chelmsford City | | 0:0 |
| |
FA Cup 1953/54, Fourth Qualifying Round |
| | | Chelmsford City | – | Great Yarmouth Town | | 0:0 |
| |
FA Cup 1952/53, Fourth Qualifying Round |
| | | Chelmsford City | – | Finchley | | 0:0 |
| |
FA Cup 1950/51, First Round Proper |
| 25.11.1950 | | Chelmsford City | – | Tonbridge | | 2:2 |
| |
FA Cup 1949/50, Second Round Proper |
| 10.12.1949 | | Chelmsford City | – | Ipswich Town | | 1:1 |
| |
