FA Cup 2023/24, Fourth Qualifying Round |
 | 14.10.2023 |  | Yeovil Town | – | Southend United | | 2:0 (1:0) |
| Yeovil |
FA Cup 2022/23, Fourth Qualifying Round |
| 15.10.2022 | | Woking | – | Southend United | | 2:1 (1:1) |
| Woking |
FA Cup 2021/22, First Round Proper |
| 06.11.2021 | | Chesterfield | – | Southend United | | 3:1 (2:1) |
| Chesterfield |
FA Cup 2019/20, First Round Proper |
| 10.11.2019 | | Dover Athletic | – | Southend United | | 1:0 (0:0) |
| River |
FA Cup 2018/19, Second Round Proper |
| 01.12.2018 | | Southend United | – | Barnsley | | 2:4 (1:1) |
| Southend-on-Sea |
FA Cup 2017/18, First Round Proper |
| 04.11.2017 | | Yeovil Town | – | Southend United | | 1:0 (1:0) |
| Yeovil |
FA Cup 2016/17, First Round Proper |
| 04.11.2016 | | Millwall | – | Southend United | | 1:0 (0:0) |
| London |
FA Cup 2015/16, First Round Proper |
| 07.11.2015 | | Scunthorpe United | – | Southend United | | 2:1 (1:1) |
| Scunthorpe |
FA Cup 2014/15, First Round Proper |
| 08.11.2014 | | Southend United | – | Chester | | 1:2 (1:1) |
| Southend-on-Sea |
FA Cup 2013/14, Fourth Round Proper |
| 25.01.2014 | | Southend United | – | Hull City | | 0:2 (0:0) |
| Southend-on-Sea |
FA Cup 2012/13, Third Round Proper |
| 15.01.2013 | | Brentford | – | Southend United | | 2:1 (1:0) * |
| Brentford |
FA Cup 2011/12, Second Round Proper |
| 13.12.2011 | | Oldham Athletic | – | Southend United | | 1:0 (0:0) * |
| Manchester |
FA Cup 2009/10, First Round Proper |
| 07.11.2009 | | Gillingham | – | Southend United | | 3:0 (2:0) |
| Gillingham |
FA Cup 2008/09, Third Round Proper |
| 14.01.2009 | | Southend United | – | Chelsea | | 1:4 (1:1) * |
| Southend-on-Sea |
FA Cup 2007/08, Fourth Round Proper |
| 25.01.2008 | | Southend United | – | Barnsley | | 0:1 (0:1) |
| Southend-on-Sea |
FA Cup 2006/07, Fourth Round Proper |
| 27.01.2007 | | Tottenham Hotspur | – | Southend United | | 3:1 (1:0) |
| London |
FA Cup 2005/06, Second Round Proper |
| 03.12.2005 | | Southend United | – | Milton Keynes Dons | | 1:2 (0:1) |
| Southend-on-Sea |
FA Cup 2004/05, First Round Proper |
| 12.11.2004 | | Southend United | – | Luton Town | | 0:3 (0:3) |
| Southend-on-Sea |
FA Cup 2003/04, Third Round Proper |
| 14.01.2004 | | Scarborough | – | Southend United | | 1:0 (0:0) * |
| Scarborough |
FA Cup 2002/03, Second Round Proper |
| 17.12.2002 | | AFC Bournemouth | – | Southend United | | 3:2 (1:2) * |
| Bournemouth |
FA Cup 2001/02, Third Round Proper |
| 08.01.2002 | | Southend United | – | Tranmere Rovers | | 1:3 (0:0) |
| Southend-on-Sea |
FA Cup 2000/01, Third Round Proper |
| 06.01.2001 | | Southend United | – | Kingstonian | | 0:1 (0:1) |
| Southend-on-Sea |
FA Cup 1999/00, First Round Proper |
| 30.10.1999 | | Torquay United | – | Southend United | | 1:0 (0:0) |
| Torquay |
FA Cup 1998/99, First Round Proper |
| 14.11.1998 | | Southend United | – | Doncaster Rovers | | 0:1 (0:1) |
| Southend-on-Sea |
FA Cup 1997/98, Second Round Proper |
| 06.12.1997 | | Fulham | – | Southend United | | 1:0 (0:0) |
| London |
FA Cup 1996/97, Third Round Proper |
| 15.01.1997 | | Leicester City | – | Southend United | | 2:0 (1:0) |
| Leicester |
FA Cup 1995/96, Third Round Proper |
| 06.01.1996 | | West Ham United | – | Southend United | | 2:0 (0:0) |
| London |
FA Cup 1994/95, Third Round Proper |
| 07.01.1995 | | Southampton | – | Southend United | | 2:0 (2:0) |
| Southampton |
FA Cup 1993/94, Third Round Proper |
| 18.01.1994 | | Luton Town | – | Southend United | | 1:0 (0:0) |
| Luton |
FA Cup 1992/93, Fifth Round Proper |
| 13.02.1993 | | Sheffield Wednesday | – | Southend United | | 2:0 (1:0) |
| Sheffield |
FA Cup 1991/92, Third Round Proper |
| 04.01.1992 | | Everton | – | Southend United | | 1:0 |
| Liverpool |
FA Cup 1990/91, First Round Proper |
| 17.11.1990 | | Leyton Orient | – | Southend United | | 3:2 |
| London |
FA Cup 1989/90, First Round Proper |
| 18.11.1989 | | Aylesbury United | – | Southend United | | 1:0 |
| Aylesbury Buckingham Road |
FA Cup 1988/89, First Round Proper |
| 19.11.1988 | | Bristol City | – | Southend United | | 3:1 (2:0) |
| Bristol |
FA Cup 1987/88, First Round Proper |
| 17.11.1987 | | Walsall | – | Southend United | | 2:1 (0:0) * |
| Walsall |
FA Cup 1986/87, Second Round Proper |
| 10.12.1986 | | Northampton Town | – | Southend United | | 3:2 (1:2) * |
| Northampton |
FA Cup 1985/86, First Round Proper |
| 16.11.1985 | | Southend United | – | Newport County |  | 0:1 |
| |
FA Cup 1984/85, First Round Proper |
| 21.11.1984 | | Colchester United | – | Southend United | | 3:2 * |
| |
FA Cup 1983/84, First Round Proper |
| 22.11.1983 | | Plymouth Argyle | – | Southend United | | 2:0 * |
| |
FA Cup 1982/83, Third Round Proper |
| 24.01.1983 | | Sheffield Wednesday | – | Southend United | | 2:1 * |
| |
FA Cup 1981/82, First Round Proper |
| 21.11.1981 | | Hereford United | – | Southend United | | 3:1 |
| |
FA Cup 1980/81, First Round Proper |
| 22.11.1980 | | Southend United | – | Hereford United | | 0:1 |
| |
FA Cup 1979/80, Second Round Proper |
| 18.12.1979 | | Harlow Town | – | Southend United | | 1:0 * |
| |
FA Cup 1978/79, Third Round Proper |
| 17.01.1979 | | Liverpool | – | Southend United | | 3:0 (1:0) * |
| Liverpool |
FA Cup 1977/78, Third Round Proper |
| 07.01.1978 | | Derby County | – | Southend United | | 3:2 |
| |
FA Cup 1976/77, Third Round Proper |
| 08.01.1977 | | Southend United | – | Chester | | 0:4 |
| Southend-on-Sea |
FA Cup 1975/76, Fifth Round Proper |
| 14.02.1976 | | Derby County | – | Southend United | | 1:0 |
| |
FA Cup 1974/75, Third Round Proper |
| 07.01.1975 | | Queens Park Rangers | – | Southend United | | 2:0 * |
| |
FA Cup 1973/74, Third Round Proper |
| 05.01.1974 | | Peterborough United | – | Southend United | | 3:1 |
| |
FA Cup 1972/73, First Round Proper |
| 18.11.1972 | | Southend United | – | Aldershot | | 0:2 |
| |
FA Cup 1971/72, Second Round Proper |
| 11.12.1971 | | Bournemouth | – | Southend United | | 2:0 |
| |
FA Cup 1970/71, Third Round Proper |
| 11.01.1971 | | Southend United | – | Carlisle United | | 0:3 |
| |
FA Cup 1969/70, First Round Proper |
| 19.11.1969 | | Gillingham | – | Southend United | | 2:1 (2:0) * |
| |
FA Cup 1968/69, Fourth Round Proper |
| 25.01.1969 | | Mansfield Town | – | Southend United | | 2:1 |
| |
FA Cup 1967/68, First Round Proper |
| 13.12.1967 | | Brighton & Hove Albion | – | Southend United | | 1:0 |
| |
FA Cup 1966/67, First Round Proper |
| 26.11.1966 | | Watford | – | Southend United | | 1:0 |
| |
FA Cup 1965/66, Third Round Proper |
| 22.01.1966 | | Rotherham United | – | Southend United | | 3:2 |
| |
FA Cup 1964/65, First Round Proper |
| 14.11.1964 | | Luton Town | – | Southend United | | 1:0 |
| |
FA Cup 1963/64, First Round Proper |
| 16.11.1963 | | Yeovil Town | – | Southend United | | 1:0 |
| |
FA Cup 1962/63, Second Round Proper |
| 24.11.1962 | | Southend United | – | Watford | | 0:2 |
| |
FA Cup 1961/62, First Round Proper |
| 04.11.1961 | | Southend United | – | Watford | | 0:2 |
| |
FA Cup 1960/61, Second Round Proper |
| 26.11.1960 | | Gillingham | – | Southend United | | 3:2 |
| |
FA Cup 1959/60, Second Round Proper |
| 05.12.1959 | | Southampton | – | Southend United | | 3:0 |
| |
FA Cup 1958/59, First Round Proper |
| 21.11.1958 | | Yeovil Town | – | Southend United | | 1:0 * |
| |
FA Cup 1957/58, Third Round Proper |
| 08.01.1958 | | Southend United | – | Liverpool | | 2:3 * |
| |
FA Cup 1956/57, Fourth Round Proper |
| 26.01.1957 | | Southend United | – | Birmingham City | | 1:6 |
| |
FA Cup 1955/56, Fourth Round Proper |
| 28.01.1956 | | Southend United | – | Manchester City | | 0:1 |
| |
FA Cup 1954/55, Third Round Proper |
| 08.01.1955 | | Everton | – | Southend United | | 3:1 |
| Liverpool |
FA Cup 1953/54, Second Round Proper |
| 12.12.1953 | | Southend United | – | Chesterfield | | 1:2 |
| |
FA Cup 1952/53, First Round Proper |
| 22.11.1952 | | Bath City | – | Southend United | | 3:1 |
| |
FA Cup 1951/52, Fifth Round Proper |
| 23.02.1952 | | Southend United | – | Sheffield United | | 1:2 |
| |
FA Cup 1950/51, First Round Proper |
| 29.11.1950 | | Southend United | – | Swindon Town | | 0:3 |
| |
FA Cup 1949/50, Third Round Proper |
| 07.01.1950 | | Blackpool | – | Southend United | | 4:0 |
| |
FA Cup 1948/49, First Round Proper |
| 04.12.1948 | | Southend United | – | Swansea Town | | 1:2 |
| |
FA Cup 1947/48, First Round Proper |
| 29.11.1947 | | Newport County | – | Southend United | | 3:2 |
| |
FA Cup 1946/47, Third Round Proper |
| 11.01.1947 | | Everton | – | Southend United | | 4:2 |
| |
FA Cup 1945/46, First Round Proper |
| 24.11.1945 | | Southend United | – | Watford | | 0:3 |
| |
FA Cup 1938/39, Fourth Round Proper |
| 21.01.1939 | | Blackburn Rovers | – | Southend United | | 4:2 |
| |
FA Cup 1937/38, Third Round Proper |
| 11.01.1938 | | Barnsley | – | Southend United | | 2:1 * |
| |
FA Cup 1936/37, Second Round Proper |
| 16.12.1936 | | York City | – | Southend United | | 2:1 * |
| |
FA Cup 1935/36, Third Round Proper |
| 15.01.1936 | | Southend United | – | Tottenham Hotspur | | 1:2 * |
| |
FA Cup 1934/35, Third Round Proper |
| 12.01.1935 | | Southend United | – | Sheffield United | | 0:4 |
| |
FA Cup 1933/34, Third Round Proper |
| 13.01.1934 | | Tranmere Rovers | – | Southend United | | 3:0 |
| |
FA Cup 1932/33, Fourth Round Proper |
| 28.01.1933 | | Southend United | – | Derby County | | 2:3 |
| |
FA Cup 1931/32, Second Round Proper |
| 12.12.1931 | | Northampton Town | – | Southend United | | 3:0 |
| |
FA Cup 1930/31, First Round Proper |
| 29.11.1930 | | Southend United | – | Torquay United | | 0:1 |
| |
FA Cup 1929/30, Second Round Proper |
| 14.12.1929 | | Southend United | – | York City | | 1:4 |
| |
FA Cup 1928/29, First Round Proper |
| 24.11.1928 | | Luton Town | – | Southend United | | 5:1 |
| |
FA Cup 1927/28, Second Round Proper |
| 10.12.1927 | | Gillingham | – | Southend United | | 2:0 |
| |
FA Cup 1926/27, Second Round Proper |
| 11.12.1926 | | Reading | – | Southend United | | 3:2 |
| |
FA Cup 1925/26, Fifth Round Proper |
| 20.02.1926 | | Southend United | – | Nottingham Forest | | 0:1 |
| |
FA Cup 1921/22, Second Round Proper |
| 28.01.1922 | | Southend United | – | Swansea Town | | 0:1 |
| |
FA Cup 1920/21, Third Round Proper |
| 19.02.1921 | | Southend United | – | Tottenham Hotspur | | 1:4 |
| |
FA Cup 1919/20, First Round Proper |
| 10.01.1920 | | Sheffield United | – | Southend United | | 3:0 |
| |
FA Cup 1914/15, Second Round Proper |
| 30.01.1915 | | Burnley | – | Southend United | | 6:0 |
| |
FA Cup 1913/14, First Round Proper |
| 10.01.1914 | | Birmingham | – | Southend United | | 2:1 |
| |
FA Cup 1912/13, First Round Proper |
| 11.01.1913 | | Chelsea | – | Southend United | | 5:2 |
| |
FA Cup 1910/11, First Round Proper |
| 14.01.1911 | | Blackburn Rovers | – | Southend United | | 5:1 |
| |
FA Cup 1909/10, Second Round Proper |
| 09.02.1910 | | Queens Park Rangers | – | Southend United | | 3:2 * |
| |
