Football League Cup 2020/21, First Round |
| 05.09.2020 | | Gillingham | | Southend United | | 1:0 (1:0) * |
| Gillingham |
Football League Cup 2019/20, Second round |
| 27.08.2019 | | Southend United | | Milton Keynes Dons | | 1:4 (0:2) |
| Southend-on-Sea |
Football League Cup 2019/20, First Round |
| 13.08.2019 | | Stevenage | | Southend United | | 1:2 (1:0) |
| Stevenage |
Football League Cup 2018/19, First Round |
| 14.08.2018 | | Southend United | | Brentford | | 2:4 (0:1) |
| Southend-on-Sea |
Football League Cup 2017/18, First Round |
| 08.08.2017 | | Southend United | | Newport County | | 0:2 (0:0) |
| Southend-on-Sea |
Football League Cup 2016/17, First Round |
| 09.08.2016 | | Southend United | | Gillingham | | 1:3 (1:0) |
| Southend-on-Sea |
Football League Cup 2015/16, First Round |
| 11.08.2015 | | Southend United | | Brighton & Hove Albion | | 0:1 (0:0) |
| Southend-on-Sea |
Football League Cup 2014/15, First Round |
| 12.08.2014 | | Southend United | | Walsall | | 1:2 (0:1) |
| Southend-on-Sea |
Football League Cup 2013/14, First Round |
| 06.08.2013 | | Southend United | | Yeovil Town | | 0:1 (0:1) |
| Southend-on-Sea |
Football League Cup 2012/13, First Round |
| 14.08.2012 | | Peterborough United | | Southend United | | 4:0 (3:0) |
| Peterborough |
Football League Cup 2011/12, First Round |
| 09.08.2011 | | Southend United | | Leyton Orient | | 1:1 aet (1:1, 1:1), pen. 3:4 |
| Southend-on-Sea |
Football League Cup 2010/11, Second round |
| 24.08.2010 | | Wolverhampton Wanderers | | Southend United | | 2:1 aet (1:0, 1:1) |
| Wolverhampton |
Football League Cup 2010/11, First Round |
| 10.08.2010 | | Southend United | | Bristol City | | 3:2 aet (1:1, 2:2) |
| Southend-on-Sea |
Football League Cup 2009/10, Second round |
| 25.08.2009 | | Hull City | | Southend United | | 3:1 (2:1) |
| Kingston upon Hull |
Football League Cup 2009/10, First Round |
| 11.08.2009 | | Cheltenham Town | | Southend United | | 1:2 (1:0) |
| Cheltenham |
Football League Cup 2008/09, First Round |
| 12.08.2008 | | Southend United | | Cheltenham Town | | 0:1 aet (0:0) |
| Southend-on-Sea |
Football League Cup 2007/08, Third round |
| 25.09.2007 | | Blackpool | | Southend United | | 2:1 aet (0:1, 1:1) |
| Blackpool |
Football League Cup 2007/08, Second round |
| 28.08.2007 | | Southend United | | Watford | | 2:0 (1:0) |
| Southend-on-Sea |
Football League Cup 2007/08, First Round |
| 14.08.2007 | | Southend United | | Cheltenham Town | | 4:1 aet (1:0, 1:1) |
| Southend-on-Sea |
Football League Cup 2006/07, Fifth Round |
| 20.12.2006 | | Tottenham Hotspur | | Southend United | | 1:0 aet (0:0) |
| London |
Football League Cup 2006/07, Fourth Round |
| 07.11.2006 | | Southend United | | Manchester United | | 1:0 (1:0) |
| Southend-on-Sea |
Football League Cup 2006/07, Third round |
| 24.10.2006 | | Leeds United | | Southend United | | 1:3 (1:2) |
| Leeds |
Football League Cup 2006/07, Second round |
| 19.09.2006 | | Southend United | | Brighton & Hove Albion | | 3:2 (0:0) |
| Southend-on-Sea |
Football League Cup 2006/07, First Round |
| 22.08.2006 | | Bournemouth | | Southend United | | 1:3 (0:1) |
| Bournemouth |
Football League Cup 2005/06, First Round |
| 22.08.2005 | | Southend United | | Southampton | | 0:3 (0:2) |
| Southend-on-Sea |
Football League Cup 2004/05, First Round |
| 23.08.2004 | | West Ham United | | Southend United | | 2:0 (1:0) |
| London |
Football League Cup 2003/04, First Round |
| 12.08.2003 | | Southend United | | Swindon Town | | 2:3 (2:1) |
| Southend-on-Sea |
Football League Cup 2002/03, First Round |
| 10.09.2002 | | Southend United | | Wimbledon | | 1:4 (0:1) |
| Southend-on-Sea |
Football League Cup 2001/02, First Round |
| 22.08.2001 | | Birmingham City | | Southend United | | 3:0 (2:0) |
| Birmingham |
Football League Cup 2000/01, First Round |
| 05.09.2000 | | Birmingham City | | Southend United | | 0:0 |
| Birmingham |
Football League Cup 2000/01, First Round |
| 22.08.2000 | | Southend United | | Birmingham City | | 0:5 (0:3) |
| Southend-on-Sea |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Oxford United | | Southend United | | 1:0 (0:0) |
| Oxford |
Football League Cup 1999/00, First Round |
| 10.08.1999 | | Southend United | | Oxford United | | 0:2 (0:0) |
| Southend-on-Sea |
Football League Cup 1998/99, Second round |
| 22.09.1998 | | Southend United | | Coventry City | | 0:4 (0:3) |
| Southend-on-Sea |
Football League Cup 1998/99, Second round |
| 16.09.1998 | | Coventry City | | Southend United | | 1:0 (0:0) |
| Coventry |
Football League Cup 1998/99, First Round |
| 18.08.1998 | | Gillingham | | Southend United | | 0:1 (0:0) |
| Gillingham |
Football League Cup 1998/99, First Round |
| 11.08.1998 | | Southend United | | Gillingham | | 1:0 (0:0) |
| Southend-on-Sea |
Football League Cup 1997/98, Second round |
| 01.10.1997 | | Derby County | | Southend United | | 5:0 (1:0) |
| Derby |
Football League Cup 1997/98, Second round |
| 16.09.1997 | | Southend United | | Derby County | | 0:1 (0:1) |
| Southend-on-Sea |
Football League Cup 1997/98, First Round |
| 26.08.1997 | | Southend United | | Cardiff City | | 3:1 (2:0) |
| Southend-on-Sea |
Football League Cup 1997/98, First Round |
| 12.08.1997 | | Cardiff City | | Southend United | | 1:1 (0:1) |
| Cardiff |
Football League Cup 1996/97, First Round |
| 03.09.1996 | | Fulham | | Southend United | | 1:2 (0:2) |
| London |
Football League Cup 1996/97, First Round |
| 20.08.1996 | | Southend United | | Fulham | | 0:2 (0:1) |
| Southend-on-Sea |
Football League Cup 1995/96, Second round |
| 03.10.1995 | | Crystal Palace | | Southend United | | 2:0 (1:0) |
| London |
Football League Cup 1995/96, Second round |
| 19.09.1995 | | Southend United | | Crystal Palace | | 2:2 (1:0) |
| Southend-on-Sea |
Football League Cup 1994/95, First Round |
| 23.08.1994 | | Watford | | Southend United | | 1:0 (1:0) |
| Watford |
Football League Cup 1994/95, First Round |
| 16.08.1994 | | Southend United | | Watford | | 0:0 |
| Southend-on-Sea |
Football League Cup 1993/94, First Round |
| 24.08.1993 | | Barnet | | Southend United | | 1:1 (0:0) |
| London |
Football League Cup 1993/94, First Round |
| 18.08.1993 | | Southend United | | Barnet | | 0:2 (0:0) |
| Southend-on-Sea |
Football League Cup 1992/93, Second round |
| 07.10.1992 | | Derby County | | Southend United | | 7:0 (3:0) |
| Derby |
Football League Cup 1992/93, Second round |
| 23.09.1992 | | Southend United | | Derby County | | 1:0 (0:0) |
| Southend-on-Sea |
Football League Cup 1991/92, First Round |
| 28.08.1991 | | Southend United | | Watford | | 1:1 (1:1) |
| Southend-on-Sea |
Football League Cup 1991/92, First Round |
| 20.08.1991 | | Watford | | Southend United | | 2:0 (2:0) |
| Watford |
Football League Cup 1990/91, Second round |
| 09.10.1990 | | Southend United | | Crystal Palace | | 1:2 |
| Southend-on-Sea |
Football League Cup 1990/91, Second round |
| 25.09.1990 | | Crystal Palace | | Southend United | | 8:0 |
| London |
Football League Cup 1990/91, First Round |
| 04.09.1990 | | Aldershot | | Southend United | | 2:2 |
| Aldershot |
Football League Cup 1990/91, First Round |
| 28.08.1990 | | Southend United | | Aldershot | | 2:1 |
| Southend-on-Sea |
Football League Cup 1989/90, Second round |
| 04.10.1989 | | Southend United | | Tottenham Hotspur | | 3:2 aet |
| Southend-on-Sea |
Football League Cup 1989/90, Second round |
| 20.09.1989 | | Tottenham Hotspur | | Southend United | | 1:0 |
| London |
Football League Cup 1989/90, First Round |
| 29.08.1989 | | Southend United | | Colchester United | | 2:1 |
| Southend-on-Sea |
Football League Cup 1989/90, First Round |
| 22.08.1989 | | Colchester United | | Southend United | | 3:4 |
| Colchester |
Football League Cup 1988/89, Second round |
| 11.10.1988 | | Southend United | | Derby County | | 1:2 |
| Southend-on-Sea |
Football League Cup 1988/89, Second round |
| 28.09.1988 | | Derby County | | Southend United | | 1:0 |
| Derby |
Football League Cup 1988/89, First Round |
| 07.09.1988 | | Brighton & Hove Albion | | Southend United | | 0:1 |
| Hove |
Football League Cup 1988/89, First Round |
| 30.08.1988 | | Southend United | | Brighton & Hove Albion | | 2:0 |
| Southend-on-Sea |
Football League Cup 1987/88, Third round |
| 27.10.1987 | | Ipswich Town | | Southend United | | 1:0 |
| Ipswich |
Football League Cup 1987/88, Second round |
| 07.10.1987 | | Derby County | | Southend United | | 0:0 |
| Derby |
Football League Cup 1987/88, Second round |
| 22.09.1987 | | Southend United | | Derby County | | 1:0 |
| Southend-on-Sea |
Football League Cup 1987/88, First Round |
| 25.08.1987 | | Southend United | | Brentford | | 4:2 |
| Southend-on-Sea |
Football League Cup 1987/88, First Round |
| 18.08.1987 | | Brentford | | Southend United | | 2:1 |
| Brentford |
Football League Cup 1986/87, Second round |
| 08.10.1986 | | Manchester City | | Southend United | | 2:1 |
| Manchester |
Football League Cup 1986/87, Second round |
| 23.09.1986 | | Southend United | | Manchester City | | 0:0 |
| Southend-on-Sea |
Football League Cup 1986/87, First Round |
| 02.09.1986 | | Brentford | | Southend United | | 2:3 |
| Brentford |
Football League Cup 1986/87, First Round |
| 26.08.1986 | | Southend United | | Brentford | | 1:0 |
| Southend-on-Sea |
Football League Cup 1985/86, First Round |
| 03.09.1985 | | Gillingham | | Southend United | | 2:0 |
| |
Football League Cup 1985/86, First Round |
| 20.08.1985 | | Southend United | | Gillingham | | 1:1 |
| |
Football League Cup 1984/85, First Round |
| 05.09.1984 | | Southend United | | Leyton Orient | | 0:0 |
| |
Football League Cup 1984/85, First Round |
| 28.08.1984 | | Leyton Orient | | Southend United | | 2:1 |
| |
Football League Cup 1983/84, First Round |
| 13.09.1983 | | Wimbledon | | Southend United | | 6:4 aet |
| |
Football League Cup 1983/84, First Round |
| 29.08.1983 | | Southend United | | Wimbledon | | 1:0 |
| |
Football League Cup 1982/83, First Round |
| 14.09.1982 | | Fulham | | Southend United | | 4:2 |
| |
Football League Cup 1982/83, First Round |
| 01.09.1982 | | Southend United | | Fulham | | 1:0 |
| |
Football League Cup 1981/82, First Round |
| 16.09.1981 | | Portsmouth | | Southend United | | 4:1 |
| |
Football League Cup 1981/82, First Round |
| 02.09.1981 | | Southend United | | Portsmouth | | 0:0 |
| |
Football League Cup 1980/81, First Round |
| 13.08.1980 | | Oxford United | | Southend United | | 2:0 |
| |
Football League Cup 1980/81, First Round |
| 09.08.1980 | | Southend United | | Oxford United | | 1:0 |
| |
Football League Cup 1979/80, Third round |
| 08.10.1979 | | West Ham United | | Southend United | | 5:1 * |
| London |
Football League Cup 1979/80, Third round |
| 01.10.1979 | | Southend United | | West Ham United | | 0:0 aet * |
| |
Football League Cup 1979/80, Third round |
| 25.09.1979 | | West Ham United | | Southend United | | 1:1 |
| London |
Football League Cup 1979/80, Second round |
| 03.09.1979 | | Southend United | | Bolton Wanderers | | 0:0 |
| |
Football League Cup 1979/80, Second round |
| 28.08.1979 | | Bolton Wanderers | | Southend United | | 1:2 |
| |
Football League Cup 1979/80, First Round |
| 21.08.1979 | | Brentford | | Southend United | | 1:4 |
| |
Football League Cup 1979/80, First Round |
| 15.08.1979 | | Southend United | | Brentford | | 2:1 |
| |
Football League Cup 1978/79, First Round |
| 15.08.1978 | | Wimbledon | | Southend United | | 4:1 |
| |
Football League Cup 1978/79, First Round |
| 12.08.1978 | | Southend United | | Wimbledon | | 1:0 |
| |
Football League Cup 1977/78, First Round |
| 16.08.1977 | | Northampton Town | | Southend United | | 2:1 |
| |
Football League Cup 1977/78, First Round |
| 13.08.1977 | | Southend United | | Northampton Town | | 2:3 |
| |
Football League Cup 1976/77, First Round |
| 17.08.1976 | | Brighton & Hove Albion | | Southend United | | 2:1 |
| |
Football League Cup 1976/77, First Round |
| 14.08.1976 | | Southend United | | Brighton & Hove Albion | | 1:1 |
| |
Football League Cup 1975/76, First Round |
| 27.08.1975 | | Peterborough United | | Southend United | | 3:0 |
| |
Football League Cup 1975/76, First Round |
| 20.08.1975 | | Southend United | | Peterborough United | | 2:0 |
| |
Football League Cup 1974/75, Second round |
| 11.09.1974 | | Southend United | | Colchester United | | 0:2 |
| |
Football League Cup 1974/75, First Round |
| 21.08.1974 | | Southend United | | Cambridge United | | 2:0 |
| |
Football League Cup 1973/74, First Round |
| 28.08.1973 | | Portsmouth | | Southend United | | 2:1 |
| |
Football League Cup 1972/73, Second round |
| 06.09.1972 | | Southend United | | Chelsea | | 0:1 |
| |
Football League Cup 1972/73, First Round |
| 16.08.1972 | | Southend United | | Aldershot | | 2:1 |
| |
Football League Cup 1971/72, First Round |
| 23.08.1971 | | Southend United | | Aldershot | | 1:2 aet * |
| |
Football League Cup 1971/72, First Round |
| 18.08.1971 | | Aldershot | | Southend United | | 1:1 |
| |
Football League Cup 1970/71, First Round |
| 17.08.1970 | | Charlton Athletic | | Southend United | | 3:0 |
| |
Football League Cup 1969/70, Third round |
| 24.09.1969 | | Bradford City | | Southend United | | 2:1 |
| |
Football League Cup 1969/70, Second round |
| 08.09.1969 | | Southend United | | Shrewsbury Town | | 2:0 * |
| |
Football League Cup 1969/70, Second round |
| 02.09.1969 | | Shrewsbury Town | | Southend United | | 2:2 |
| |
Football League Cup 1969/70, First Round |
| 21.08.1969 | | Brentford | | Southend United | | 2:3 aet * |
| |
Football League Cup 1969/70, First Round |
| 18.08.1969 | | Brentford | | Southend United | | 0:0 aet * |
| |
Football League Cup 1969/70, First Round |
| 12.08.1969 | | Southend United | | Brentford | | 2:2 |
| |
Football League Cup 1968/69, Second round |
| 04.09.1968 | | Wolverhampton Wanderers | | Southend United | | 1:0 |
| |
Football League Cup 1968/69, First Round |
| 13.08.1968 | | Bournemouth & Boscombe Athletic | | Southend United | | 1:6 |
| |
Football League Cup 1967/68, Second round |
| 13.09.1967 | | Southend United | | Darlington | | 1:2 |
| |
Football League Cup 1967/68, First Round |
| 23.08.1967 | | Southend United | | Brentford | | 1:0 |
| |
Football League Cup 1966/67, First Round |
| 31.08.1966 | | Gillingham | | Southend United | | 2:0 aet * |
| |
Football League Cup 1966/67, First Round |
| 24.08.1966 | | Southend United | | Gillingham | | 0:0 |
| |
Football League Cup 1965/66, Second round |
| 22.09.1965 | | Reading | | Southend United | | 5:1 |
| |
Football League Cup 1965/66, First Round |
| 06.09.1965 | | Southend United | | Newport County | | 3:1 * |
| |
Football League Cup 1965/66, First Round |
| 01.09.1965 | | Newport County | | Southend United | | 2:2 |
| |
Football League Cup 1964/65, Third round |
| 14.10.1964 | | Stoke City | | Southend United | | 3:1 |
| |
Football League Cup 1964/65, Second round |
| 28.09.1964 | | Southend United | | Hull City | | 3:1 * |
| |
Football League Cup 1964/65, Second round |
| 22.09.1964 | | Hull City | | Southend United | | 0:0 |
| |
Football League Cup 1964/65, First Round |
| 02.09.1964 | | Brentford | | Southend United | | 0:2 |
| |
Football League Cup 1963/64, Third round |
| 16.10.1963 | | Swindon Town | | Southend United | | 3:0 |
| |
Football League Cup 1963/64, Second round |
| 25.09.1963 | | Southend United | | Port Vale | | 2:1 |
| |
Football League Cup 1962/63, Second round |
| 26.09.1962 | | Southend United | | Notts County | | 2:3 |
| |
Football League Cup 1961/62, First Round |
| 13.09.1961 | | Southend United | | Stoke City | | 0:1 |
| |
Football League Cup 1960/61, Second round |
| 25.10.1960 | | Rochdale | | Southend United | | 5:2 |
| |