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 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 2010/11, Second round |
| 24.08.2010 | | Wolverhampton Wanderers | – | Southend United | | 2:1 aet
(1:0, 1:1) |
| Wolverhampton |
Football League Cup 2009/10, Second round |
| 25.08.2009 | | Hull City | – | Southend United | | 3:1 (2:1) |
| Kingston upon Hull |
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 2006/07, Fifth Round |
| 20.12.2006 | | Tottenham Hotspur | – | Southend United | | 1:0 aet
(0:0) |
| London |
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 |
| 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 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 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 1994/95, First Round |
| 23.08.1994 | | Watford | – | Southend United | | 1:0 (1:0) |
| Watford |
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 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 1989/90, Second round |
| 20.09.1989 | | Tottenham Hotspur | – | Southend United | | 1:0 |
| London |
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 1987/88, Third round |
| 27.10.1987 | | Ipswich Town | – | Southend United | | 1:0 |
| Ipswich |
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 1985/86, First Round |
| 03.09.1985 | | Gillingham | – | Southend United | | 2:0 |
| |
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 1982/83, First Round |
| 14.09.1982 | | Fulham | – | Southend United | | 4:2 |
| |
Football League Cup 1981/82, First Round |
| 16.09.1981 | | Portsmouth | – | Southend United | | 4:1 |
| |
Football League Cup 1980/81, First Round |
| 13.08.1980 | | Oxford United | – | Southend United | | 2:0 |
| |
Football League Cup 1979/80, Third round |
| 08.10.1979 | | West Ham United | – | Southend United | | 5:1 * |
| London |
Football League Cup 1978/79, First Round |
| 15.08.1978 | | Wimbledon | – | Southend United | | 4:1 |
| |
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 1975/76, First Round |
| 27.08.1975 | | Peterborough United | – | Southend United | | 3:0 |
| |
Football League Cup 1974/75, Second round |
| 11.09.1974 | | Southend United | – | Colchester United | | 0:2 |
| |
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 1971/72, First Round |
| 23.08.1971 | | Southend United | – | Aldershot | | 1:2 aet * |
| |
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 1968/69, Second round |
| 04.09.1968 | | Wolverhampton Wanderers | – | Southend United | | 1:0 |
| |
Football League Cup 1967/68, Second round |
| 13.09.1967 | | Southend United | – | Darlington | | 1:2 |
| |
Football League Cup 1966/67, First Round |
| 31.08.1966 | | Gillingham | – | Southend United | | 2:0 aet * |
| |
Football League Cup 1965/66, Second round |
| 22.09.1965 | | Reading | – | Southend United | | 5:1 |
| |
Football League Cup 1964/65, Third round |
| 14.10.1964 | | Stoke City | – | Southend United | | 3:1 |
| |
Football League Cup 1963/64, Third round |
| 16.10.1963 | | Swindon Town | – | Southend United | | 3:0 |
| |
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 |
| |
