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 2000/01, First Round |
| 05.09.2000 | | Birmingham City | – | Southend United | | 0:0 |
| Birmingham |
Football League Cup 1997/98, First Round |
| 12.08.1997 |  | Cardiff City | – | Southend United | | 1:1 (0:1) |
| Cardiff |
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 |
| 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 1991/92, First Round |
| 28.08.1991 | | Southend United | – | Watford | | 1:1 (1:1) |
| Southend-on-Sea |
Football League Cup 1990/91, First Round |
| 04.09.1990 | | Aldershot | – | Southend United | | 2:2 |
| Aldershot |
Football League Cup 1987/88, Second round |
| 07.10.1987 | | Derby County | – | Southend United | | 0:0 |
| Derby |
Football League Cup 1986/87, Second round |
| 23.09.1986 | | Southend United | – | Manchester City | | 0:0 |
| Southend-on-Sea |
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 1981/82, First Round |
| 02.09.1981 | | Southend United | – | Portsmouth | | 0:0 |
| |
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 1976/77, First Round |
| 14.08.1976 | | Southend United | – | Brighton & Hove Albion | | 1:1 |
| |
Football League Cup 1971/72, First Round |
| 18.08.1971 | | Aldershot | – | Southend United | | 1:1 |
| |
Football League Cup 1969/70, Second round |
| 02.09.1969 | | Shrewsbury Town | – | Southend United | | 2:2 |
| |
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 1966/67, First Round |
| 24.08.1966 | | Southend United | – | Gillingham | | 0:0 |
| |
Football League Cup 1965/66, First Round |
| 01.09.1965 | | Newport County | – | Southend United | | 2:2 |
| |
Football League Cup 1964/65, Second round |
| 22.09.1964 | | Hull City | – | Southend United | | 0:0 |
| |
