Football League Cup 2019/20, First Round |
 | 13.08.2019 |  | Stevenage | – | Southend United | | 1:2 (1:0) |
| Stevenage |
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, First Round |
| 11.08.2009 | | Cheltenham Town | – | Southend United | | 1:2 (1:0) |
| Cheltenham |
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, 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 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, First Round |
| 26.08.1997 | | Southend United | – | Cardiff City |  | 3:1 (2:0) |
| Southend-on-Sea |
Football League Cup 1996/97, First Round |
| 03.09.1996 | | Fulham | – | Southend United | | 1:2 (0:2) |
| London |
Football League Cup 1992/93, Second round |
| 23.09.1992 | | Southend United | – | Derby County | | 1:0 (0:0) |
| Southend-on-Sea |
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, 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, 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, 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 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 1983/84, First Round |
| 29.08.1983 | | Southend United | – | Wimbledon | | 1:0 |
| |
Football League Cup 1982/83, First Round |
| 01.09.1982 | | Southend United | – | Fulham | | 1:0 |
| |
Football League Cup 1980/81, First Round |
| 09.08.1980 | | Southend United | – | Oxford United | | 1:0 |
| |
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 |
| 12.08.1978 | | Southend United | – | Wimbledon | | 1:0 |
| |
Football League Cup 1975/76, First Round |
| 20.08.1975 | | Southend United | – | Peterborough United | | 2:0 |
| |
Football League Cup 1974/75, First Round |
| 21.08.1974 | | Southend United | – | Cambridge United | | 2:0 |
| |
Football League Cup 1972/73, First Round |
| 16.08.1972 | | Southend United | – | Aldershot | | 2:1 |
| |
Football League Cup 1969/70, Second round |
| 08.09.1969 | | Southend United | – | Shrewsbury Town | | 2:0 * |
| |
Football League Cup 1969/70, First Round |
| 21.08.1969 | | Brentford | – | Southend United | | 2:3 aet * |
| |
Football League Cup 1968/69, First Round |
| 13.08.1968 | | Bournemouth & Boscombe Athletic | – | Southend United | | 1:6 |
| |
Football League Cup 1967/68, First Round |
| 23.08.1967 | | Southend United | – | Brentford | | 1:0 |
| |
Football League Cup 1965/66, First Round |
| 06.09.1965 | | Southend United | – | Newport County | | 3:1 * |
| |
Football League Cup 1964/65, Second round |
| 28.09.1964 | | Southend United | – | Hull City | | 3:1 * |
| |
Football League Cup 1964/65, First Round |
| 02.09.1964 | | Brentford | – | Southend United | | 0:2 |
| |
Football League Cup 1963/64, Second round |
| 25.09.1963 | | Southend United | – | Port Vale | | 2:1 |
| |
