FA Cup 2023/24, Third Qualifying Round |
 | 02.10.2023 |  | Chelmsford City | – | Bromsgrove Sporting | | 3:0 (1:0) * |
| Chelmsford |
FA Cup 2023/24, Second Qualifying Round |
| 18.09.2023 | | Chelmsford City | – | Ware | | 2:1 (1:1) * |
| Chelmsford |
FA Cup 2022/23, Fourth Qualifying Round |
| 15.10.2022 | | Chelmsford City | – | Aldershot Town | | 2:0 (1:0) |
| Chelmsford |
FA Cup 2022/23, Third Qualifying Round |
| 01.10.2022 | | Romford | – | Chelmsford City | | 0:5 (0:0) |
| Aveley |
FA Cup 2022/23, Second Qualifying Round |
| 17.09.2022 | | Chelmsford City | – | Kings Langley | | 6:1 (5:1) |
| Chelmsford |
FA Cup 2021/22, Third qualifying round |
| 02.10.2021 | | Chelmsford City | – | Enfield Town | | 1:0 (0:0) |
| Chelmsford |
FA Cup 2021/22, Second qualifying round |
| 18.09.2021 | | Chelmsford City | – | Little Oakley | | 2:1 (1:0) |
| Chelmsford |
FA Cup 2017/18, Fourth Qualifying Round |
| 16.10.2017 | | Chelmsford City | – | Bath City | | 1:0 (0:0) * |
| Chelmsford |
FA Cup 2017/18, Third Qualifying Round |
| 30.09.2017 | | Chelmsford City | – | Weymouth | | 2:1 (0:0) |
| Chelmsford |
FA Cup 2017/18, Second Qualifying Round |
| 16.09.2017 | | Chelmsford City | – | Ramsgate | | 7:0 (2:0) |
| Chelmsford |
FA Cup 2015/16, Second Qualifying Round |
| 29.09.2015 | | Ebbsfleet United | – | Chelmsford City | | 1:2 (1:1) * |
| Northfleet |
FA Cup 2014/15, Third Qualifying Round |
| 13.10.2014 | | Chelmsford City | – | Whitehawk | | 4:1 (2:1) * |
| Chelmsford |
FA Cup 2014/15, Second Qualifying Round |
| 27.09.2014 | | Chelmsford City | – | Worthing | | 6:0 (3:0) |
| Chelmsford |
FA Cup 2012/13, First Round Proper |
| 03.11.2012 | | Chelmsford City | – | Colchester United | | 3:1 (1:0) |
| Chelmsford |
FA Cup 2012/13, Third Qualifying Round |
| 06.10.2012 | | Cray Wanderers | – | Chelmsford City | | 1:2 (1:0) |
| London |
FA Cup 2012/13, Second Qualifying Round |
| 22.09.2012 | | Chelmsford City | – | Leatherhead | | 2:1 |
| Chelmsford |
FA Cup 2011/12, First Round Proper |
| 12.11.2011 | | Chelmsford City | – | A.F.C. Telford United | | 4:0 (2:0) |
| Chelmsford |
FA Cup 2011/12, Fourth Qualifying Round |
| 01.11.2011 | | Gloucester City | – | Chelmsford City | | 0:1 (0:0) * |
| Cheltenham |
FA Cup 2011/12, Third qualifying round |
| 15.10.2011 | | Lowestoft Town | – | Chelmsford City | | 2:5 |
| Lowestoft |
FA Cup 2011/12, Second Qualifying Round |
| 01.10.2011 | | Chelmsford City | – | Tonbridge Angels | | 3:0 |
| |
FA Cup 2010/11, First Round Proper |
| 06.11.2010 | | Chelmsford City | – | Hendon | | 3:2 (2:1) |
| Chelmsford |
FA Cup 2010/11, Fourth Qualifying Round |
| 25.10.2010 | | Chelmsford City | – | Carshalton Athletic | | 3:2 (0:0) * |
| |
FA Cup 2010/11, Third Qualifying Round |
| 12.10.2010 | | Bromley | – | Chelmsford City | | 0:3 * |
| |
FA Cup 2010/11, Second Qualifying Round |
| 25.09.2010 | | Chelmsford City | – | Chertsey Town | | 7:0 |
| |
FA Cup 2009/10, Third Qualifying Round |
| 10.10.2009 | | Dartford | – | Chelmsford City | | 1:4 |
| |
FA Cup 2009/10, Second Qualifying Round |
| 26.09.2009 | | Enfield 1893 | – | Chelmsford City | | 0:5 |
| |
FA Cup 2007/08, Second Qualifying Round |
| 29.09.2007 | | Hemel Hempstead Town | – | Chelmsford City | | 0:2 |
| |
FA Cup 2007/08, First Qualifying Round |
| 15.09.2007 | | Chelmsford City | – | Burnham Ramblers | | 5:0 |
| |
FA Cup 2006/07, Fourth Qualifying Round |
| 28.10.2006 | | Chelmsford City | – | Gravesend & Northfleet | | 1:0 (1:0) |
| |
FA Cup 2006/07, Third Qualifying Round |
| 14.10.2006 | | Rugby Town | – | Chelmsford City | | 1:3 |
| |
FA Cup 2006/07, Second Qualifying Round |
| 02.10.2006 | | Chelmsford City | – | Dereham Town | | 4:0 * |
| |
FA Cup 2006/07, First Qualifying Round |
| 16.09.2006 | | Barking | – | Chelmsford City | | 1:4 |
| |
FA Cup 2005/06, Second Qualifying Round |
| 24.09.2005 | | Chelmsford City | – | Dover Athletic | | 1:0 |
| |
FA Cup 2005/06, First Qualifying Round |
| 14.09.2005 | | Harlow Town | – | Chelmsford City | | 0:1 * |
| |
FA Cup 2002/03, Second Qualifying Round |
| | | Chelmsford City | – | Carshalton Athletic | | 1:0 * |
| |
FA Cup 2001/02, Second Qualifying Round |
| | | Braintree Town | – | Chelmsford City | | 0:1 |
| |
FA Cup 2000/01, First Qualifying Round |
| | | Tilbury | – | Chelmsford City | | 1:3 |
| |
FA Cup 2000/01, Preliminary Round |
| | | Chelmsford City | – | Sawbridgeworth | | 3:1 |
| |
FA Cup 1999/00, Fourth Qualifying Round |
| | | Horsham YMCA | – | Chelmsford City | | 2:3 (1:2) |
| |
FA Cup 1999/00, Third Qualifying Round |
| | | Chelmsford City | – | Moor Green | | 1:0 |
| |
FA Cup 1999/00, Second Qualifying Round |
| | | Aylesbury United | – | Chelmsford City | | 1:3 |
| |
FA Cup 1999/00, First Qualifying Round |
| | | Kingsbury Town | – | Chelmsford City | | 0:1 |
| |
FA Cup 1999/00, Preliminary Round |
| | | Woodbridge Town | – | Chelmsford City | | 1:5 |
| |
FA Cup 1998/99, First Qualifying Round |
| | | Northampton Spencer | – | Chelmsford City | | 1:4 |
| |
FA Cup 1998/99, Preliminary Round |
| | | Chelmsford City | – | Fakenham Town | | 6:0 |
| |
FA Cup 1996/97, Second Qualifying Round |
| | | Chelmsford City | – | Heybridge Swifts | | 2:1 * |
| |
FA Cup 1996/97, First Qualifying Round |
| | | Chelmsford City | – | March Town United | | 5:0 |
| |
FA Cup 1995/96, Second Qualifying Round |
| | | Chelmsford City | – | Holbeach United | | 3:1 * |
| |
FA Cup 1995/96, First Qualifying Round |
| | | Chelmsford City | – | Collier Row | | 1:0 |
| |
FA Cup 1994/95, Fourth Qualifying Round |
| | | Chelmsford City | – | Valley Sports Rugby | | 2:1 * |
| |
FA Cup 1994/95, Third Qualifying Round |
| | | Hendon | – | Chelmsford City | | 0:1 |
| |
FA Cup 1994/95, Second Qualifying Round |
| | | Chelmsford City | – | Witham Town | | 1:0 |
| |
FA Cup 1994/95, First Qualifying Round |
| | | Chelmsford City | – | Barton Rovers | | 1:0 |
| |
FA Cup 1993/94, Second Qualifying Round |
| | | Chelmsford City | – | Stamford | | 5:2 |
| |
FA Cup 1993/94, First Qualifying Round |
| | | Chelmsford City | – | Newmarket Town | | 3:0 * |
| |
FA Cup 1991/92, First Qualifying Round |
| | | Clapton | – | Chelmsford City | | 1:5 |
| |
FA Cup 1990/91, Fourth Qualifying Round |
| | | Kettering Town | – | Chelmsford City | | 1:2 * |
| |
FA Cup 1990/91, Third Qualifying Round |
| | | Chelmsford City | – | Enfield | | 1:0 * |
| |
FA Cup 1990/91, Second Qualifying Round |
| | | Hornchurch | – | Chelmsford City | | 1:2 |
| |
FA Cup 1990/91, First Qualifying Round |
| | | Walthamstow Pennant | – | Chelmsford City | | 0:3 |
| |
FA Cup 1987/88, Fourth Qualifying Round |
| | | Letchworth Garden City | – | Chelmsford City | | 0:1 |
| |
FA Cup 1986/87, First Round Proper |
| 17.11.1986 | | Chelmsford City | – | Woking | | 2:1 (1:0) * |
| |
FA Cup 1986/87, Fourth Qualifying Round |
| | | Chelmsford City | – | Kidderminster Harriers | | 2:1 |
| |
FA Cup 1985/86, First Round Proper |
| 16.11.1985 | | Chelmsford City | – | Weymouth | | 1:0 |
| |
FA Cup 1985/86, Fourth Qualifying Round |
| | | Chelmsford City | – | Kettering Town | | 1:0 |
| |
FA Cup 1985/86, Third Qualifying Round |
| | | Chelmsford City | – | Ware | | 1:0 |
| |
FA Cup 1985/86, Second Qualifying Round |
| | | Chelmsford City | – | Buckingham Town | | 1:0 |
| |
FA Cup 1985/86, First Qualifying Round |
| | | Chelmsford City | – | Alma Swanley | | 2:0 |
| |
FA Cup 1984/85, Second Qualifying Round |
| | | Chelmsford City | – | Hornchurch | | 6:1 * |
| |
FA Cup 1984/85, First Qualifying Round |
| | | Royston Town | – | Chelmsford City | | 0:3 |
| |
FA Cup 1983/84, First Round Proper |
| 22.11.1983 | | Wycombe Wanderers | – | Chelmsford City | | 1:2 * |
| |
FA Cup 1983/84, Fourth Qualifying Round |
| | | Chelmsford City | – | Bedworth United | | 2:1 |
| |
FA Cup 1983/84, Third Qualifying Round |
| | | Valley Sports Rugby | – | Chelmsford City | | 1:2 * |
| |
FA Cup 1983/84, Second Qualifying Round |
| | | Chelmsford City | – | Great Yarmouth Town | | 4:2 |
| |
FA Cup 1983/84, First Qualifying Round |
| | | Chelmsford City | – | Gorleston | | 5:1 |
| |
FA Cup 1982/83, Third Qualifying Round |
| | | Chelmsford City | – | Leytonstone/Ilford | | 2:1 * |
| |
FA Cup 1982/83, Second Qualifying Round |
| | | Chelmsford City | – | Grays Athletic | | 3:2 |
| |
FA Cup 1982/83, First Qualifying Round |
| | | Chelmsford City | – | Sudbury Town | | 3:1 * |
| |
FA Cup 1982/83, Preliminary Round |
| | | Chelmsford City | – | Finchley | | 3:1 |
| |
FA Cup 1980/81, Second Qualifying Round |
| | | Chelmsford City | – | Edgware Town | | 3:1 |
| |
FA Cup 1980/81, First Qualifying Round |
| | | Clacton Town | – | Chelmsford City | | 1:2 * |
| |
FA Cup 1979/80, Preliminary Round |
| | | Great Yarmouth Town | – | Chelmsford City | | 1:3 |
| |
FA Cup 1977/78, Third Qualifying Round |
| | | Chelmsford City | – | Harlow Town | | 2:1 * |
| |
FA Cup 1977/78, Second Qualifying Round |
| | | Chelmsford City | – | Gorleston | | 5:0 * |
| |
FA Cup 1977/78, First Qualifying Round |
| | | Histon | – | Chelmsford City | | 0:1 |
| |
FA Cup 1974/75, Fourth Qualifying Round |
| | | Horsham | – | Chelmsford City | | 1:3 |
| |
FA Cup 1973/74, Fourth Qualifying Round |
| | | Epping Town | – | Chelmsford City | | 1:2 |
| |
FA Cup 1972/73, Second Round Proper |
| 09.12.1972 | | Chelmsford City | – | Telford United | | 5:0 |
| |
FA Cup 1972/73, First Round Proper |
| 18.11.1972 | | Chelmsford City | – | Hillingdon Borough | | 2:0 |
| |
FA Cup 1972/73, Fourth Qualifying Round |
| | | Crawley Town | – | Chelmsford City | | 0:2 |
| |
FA Cup 1970/71, First Round Proper |
| 23.11.1970 | | Chelmsford City | – | Crawley Town | | 6:1 * |
| |
FA Cup 1970/71, Fourth Qualifying Round |
| | | Chelmsford City | – | King's Lynn | | 2:0 |
| |
FA Cup 1969/70, Fourth Qualifying Round |
| | | Chelmsford City | – | Cambridge United | | 3:2 |
| |
FA Cup 1968/69, Fourth Qualifying Round |
| | | Chelmsford City | – | Kingstonian | | 5:3 * |
| |
FA Cup 1967/68, First Round Proper |
| 18.12.1967 | | Chelmsford City | – | Oxford United | | 1:0 * |
| London |
FA Cup 1967/68, Fourth Qualifying Round |
| | | Chelmsford City | – | Banbury United | | 2:0 |
| |
FA Cup 1966/67, Fourth Qualifying Round |
| | | Hornchurch | – | Chelmsford City | | 0:4 |
| |
FA Cup 1964/65, Fourth Qualifying Round |
| | | Chelmsford City | – | Oxford City | | 6:2 |
| |
FA Cup 1963/64, First Round Proper |
| 16.11.1963 | | Cambridge United | – | Chelmsford City | | 0:1 |
| |
FA Cup 1963/64, Fourth Qualifying Round |
| | | Chelmsford City | – | Romford | | 2:0 |
| |
FA Cup 1962/63, Fourth Qualifying Round |
| | | Chelmsford City | – | Romford | | 2:0 |
| |
FA Cup 1961/62, Fourth Qualifying Round |
| | | Chelmsford City | – | Wisbech Town | | 1:0 * |
| |
FA Cup 1960/61, Fourth Qualifying Round |
| | | Wisbech Town | – | Chelmsford City | | 1:4 * |
| |
FA Cup 1959/60, Fourth Qualifying Round |
| | | Grays Athletic | – | Chelmsford City | | 1:3 |
| |
FA Cup 1958/59, Fourth Qualifying Round |
| | | Chelmsford City | – | Harwich & Parkeston | | 2:0 |
| |
FA Cup 1957/58, Third Qualifying Round |
| | | Chelmsford City | – | Rainham Town | | 6:0 |
| |
FA Cup 1957/58, Second Qualifying Round |
| | | Chelmsford City | – | Leyton | | 5:0 |
| |
FA Cup 1957/58, First Qualifying Round |
| | | Chelmsford City | – | Clacton Town | | 4:0 |
| |
FA Cup 1957/58, Preliminary Round |
| | | Chelmsford City | – | Briggs Sports | | 3:0 |
| |
FA Cup 1956/57, Second Qualifying Round |
| | | Chelmsford City | – | Romford | | 4:0 |
| |
FA Cup 1956/57, First Qualifying Round |
| | | Chelmsford City | – | Rainham Town | | 6:0 |
| |
FA Cup 1956/57, Preliminary Round |
| | | Chelmsford City | – | Ilford | | 1:0 |
| |
FA Cup 1954/55, Fourth Qualifying Round |
| | | Gorleston | – | Chelmsford City | | 1:2 |
| |
FA Cup 1954/55, Third Qualifying Round |
| | | Leyton | – | Chelmsford City | | 0:1 |
| |
FA Cup 1954/55, Second Qualifying Round |
| | | Chelmsford City | – | Barking | | 3:2 * |
| |
FA Cup 1954/55, First Qualifying Round |
| | | Chelmsford City | – | Leytonstone | | 2:1 * |
| |
FA Cup 1954/55, Preliminary Round |
| | | Chelmsford City | – | Clacton Town | | 2:0 |
| |
FA Cup 1953/54, Third Qualifying Round |
| | | Chelmsford City | – | Briggs Sports | | 1:0 |
| |
FA Cup 1953/54, Second Qualifying Round |
| | | Chelmsford City | – | Erith & Belvedere | | 2:1 |
| |
FA Cup 1953/54, First Qualifying Round |
| | | Chelmsford City | – | Romford | | 3:2 |
| |
FA Cup 1953/54, Preliminary Round |
| | | Woodford Town | – | Chelmsford City | | 0:3 |
| |
FA Cup 1950/51, First Round Proper |
| 29.11.1950 | | Tonbridge | – | Chelmsford City | | 0:1 * |
| |
FA Cup 1950/51, Fourth Qualifying Round |
| | | Wycombe Wanderers | – | Chelmsford City | | 0:4 |
| |
FA Cup 1949/50, First Round Proper |
| 26.11.1949 | | Leytonstone | – | Chelmsford City | | 1:2 |
| |
FA Cup 1949/50, Fourth Qualifying Round |
| | | Barnet | – | Chelmsford City | | 2:6 |
| |
FA Cup 1948/49, Fourth Qualifying Round |
| | | Guildford City | – | Chelmsford City | | 0:2 |
| |
FA Cup 1945/46, Fourth Qualifying Round |
| | | Chelmsford City | – | Leiston | | 9:0 |
| |
FA Cup 1938/39, Third Round Proper |
| 07.01.1939 | | Chelmsford City | – | Southampton | | 4:1 |
| |
FA Cup 1938/39, Second Round Proper |
| 10.12.1938 | | Chelmsford City | – | Darlington | | 3:1 |
| |
FA Cup 1938/39, First Round Proper |
| 26.11.1938 | | Chelmsford City | – | Kidderminster Harriers | | 4:0 |
| |
