Football League Cup 2023/24, First Round |
 | 08.08.2023 |  | Plymouth Argyle | – | Leyton Orient | | 2:0 (2:0) |
| Plymouth |
Football League Cup 2022/23, First Round |
| 09.08.2022 | | Forest Green Rovers | – | Leyton Orient | | 2:0 (1:0) |
| Nailsworth |
Football League Cup 2020/21, Third round |
| 22.09.2020 | | Leyton Orient | – | Tottenham Hotspur | | -:+ |
| London |
Football League Cup 2019/20, First Round |
| 13.08.2019 | | Plymouth Argyle | – | Leyton Orient | | 2:0 (0:0) |
| Plymouth |
Football League Cup 2016/17, First Round |
| 09.08.2016 | | Leyton Orient | – | Fulham | | 2:3 (0:1) |
| London |
Football League Cup 2015/16, First Round |
| 11.08.2015 | | Milton Keynes Dons | – | Leyton Orient | | 2:1 (0:1) |
| Milton Keynes |
Football League Cup 2014/15, Third round |
| 23.09.2014 | | Leyton Orient | – | Sheffield United | | 0:1 (0:1) |
| London |
Football League Cup 2013/14, Second round |
| 27.08.2013 | | Leyton Orient | – | Hull City | | 0:1 aet
(0:0) |
| London |
Football League Cup 2012/13, Second round |
| 29.08.2012 | | Everton | – | Leyton Orient | | 5:0 (4:0) |
| Liverpool |
Football League Cup 2011/12, Third round |
| 20.09.2011 | | Blackburn Rovers | – | Leyton Orient | | 3:2 (1:0) |
| Blackburn |
Football League Cup 2010/11, Second round |
| 24.08.2010 | | Leyton Orient | – | West Bromwich Albion | | 0:2 (0:1) |
| London |
Football League Cup 2009/10, Second round |
| 26.08.2009 | | Leyton Orient | – | Stoke City | | 0:1 aet
(0:0) |
| London |
Football League Cup 2008/09, First Round |
| 12.08.2008 | | Ipswich Town | – | Leyton Orient | | 4:1 (3:0) |
| Ipswich |
Football League Cup 2007/08, Second round |
| 28.08.2007 |  | Cardiff City | – | Leyton Orient | | 1:0 (0:0) |
| Cardiff |
Football League Cup 2006/07, First Round |
| 24.08.2006 | | Leyton Orient | – | West Bromwich Albion | | 0:3 (0:1) |
| London |
Football League Cup 2005/06, First Round |
| 23.08.2005 | | Leyton Orient | – | Luton Town | | 1:3 (0:1) |
| London |
Football League Cup 2004/05, First Round |
| 24.08.2004 | | Leyton Orient | – | Bournemouth | | 1:3 (1:1) |
| London |
Football League Cup 2003/04, First Round |
| 12.08.2003 | | Cardiff City | – | Leyton Orient | | 4:1 (2:0) |
| Cardiff |
Football League Cup 2002/03, Second round |
| 02.10.2002 | | Leyton Orient | – | Birmingham City | | 2:3 (0:2) |
| London |
Football League Cup 2001/02, First Round |
| 21.08.2001 | | Leyton Orient | – | Crystal Palace | | 2:4 (2:1) |
| London |
Football League Cup 2000/01, Second round |
| 20.09.2000 | | Newcastle United | – | Leyton Orient | | 2:0 (1:0) |
| Newcastle upon Tyne |
Football League Cup 1999/00, Second round |
| 14.09.1999 | | Grimsby Town | – | Leyton Orient | | 4:1 (2:1) |
| Cleethorpes |
Football League Cup 1998/99, Second round |
| 15.09.1998 | | Leyton Orient | – | Nottingham Forest | | 1:5 (0:4) |
| London |
Football League Cup 1997/98, Second round |
| 16.09.1997 | | Leyton Orient | – | Bolton Wanderers | | 1:3 (1:2) |
| London |
Football League Cup 1996/97, First Round |
| 20.08.1996 | | Portsmouth | – | Leyton Orient | | 2:0 (1:0) |
| Portsmouth |
Football League Cup 1995/96, First Round |
| 15.08.1995 | | Wycombe Wanderers | – | Leyton Orient | | 3:0 (2:0) |
| High Wycombe |
Football League Cup 1994/95, First Round |
| 16.08.1994 | | Barnet | – | Leyton Orient | | 4:0 (0:0) |
| London |
Football League Cup 1993/94, First Round |
| 24.08.1993 | | Wycombe Wanderers | – | Leyton Orient | | 1:0 (1:0) |
| High Wycombe |
Football League Cup 1993/94, First Round |
| 17.08.1993 | | Leyton Orient | – | Wycombe Wanderers | | 0:2 (0:1) |
| London |
Football League Cup 1992/93, First Round |
| 26.08.1992 | | Millwall | – | Leyton Orient | | 3:0 (2:0) |
| London |
Football League Cup 1991/92, Second round |
| 09.10.1991 | | Sheffield Wednesday | – | Leyton Orient | | 4:1 (0:1) |
| Sheffield |
Football League Cup 1991/92, First Round |
| 10.09.1991 | | Northampton Town | – | Leyton Orient | | 2:0 (1:0) |
| Northampton |
Football League Cup 1990/91, Third round |
| 07.11.1990 | | Leyton Orient | – | Crystal Palace | | 0:1 * |
| London |
Football League Cup 1989/90, Second round |
| 19.09.1989 | | Leyton Orient | – | Everton | | 0:2 |
| London |
Football League Cup 1988/89, Third round |
| 01.11.1988 | | Ipswich Town | – | Leyton Orient | | 2:0 |
| Ipswich |
Football League Cup 1988/89, Second round |
| 27.09.1988 | | Leyton Orient | – | Stoke City | | 1:2 |
| London |
Football League Cup 1987/88, First Round |
| 25.08.1987 | | Millwall | – | Leyton Orient | | 1:0 |
| London |
Football League Cup 1986/87, First Round |
| 02.09.1986 | | Cambridge United | – | Orient | | 1:0 |
| Cambridge |
Football League Cup 1985/86, Second round |
| 30.10.1985 | | Tottenham Hotspur | – | Leyton Orient | | 4:0 |
| London |
Football League Cup 1984/85, Second round |
| 09.10.1984 | | Luton Town | – | Leyton Orient | | 3:1 |
| |
Football League Cup 1984/85, Second round |
| 25.09.1984 | | Leyton Orient | – | Luton Town | | 1:4 |
| |
Football League Cup 1983/84, First Round |
| 30.08.1983 | | Aldershot | – | Leyton Orient | | 3:1 |
| |
Football League Cup 1982/83, First Round |
| 31.08.1982 | | Gillingham | – | Leyton Orient | | 3:0 |
| |
Football League Cup 1981/82, First Round |
| 16.09.1981 | | Millwall | – | Leyton Orient | | 3:2 |
| |
Football League Cup 1980/81, Second round |
| 03.09.1980 | | Tottenham Hotspur | – | Leyton Orient | | 3:1 |
| London |
Football League Cup 1980/81, Second round |
| 27.08.1980 | | Leyton Orient | – | Tottenham Hotspur | | 0:1 |
| |
Football League Cup 1978/79, Second round |
| 29.08.1978 | | Orient | – | Chesterfield | | 1:2 |
| |
Football League Cup 1977/78, Second round |
| 31.08.1977 | | Derby County | – | Leyton Orient | | 3:1 |
| |
Football League Cup 1977/78, First Round |
| 16.08.1977 | | Leyton Orient | – | Fulham | | 1:2 |
| |
Football League Cup 1976/77, Third round |
| 19.10.1976 | | Millwall | – | Orient | | 3:0 * |
| |
Football League Cup 1975/76, Second round |
| 09.09.1975 | | Birmingham City | – | Orient | | 4:0 |
| |
Football League Cup 1974/75, Second round |
| 17.09.1974 | | Orient | – | Queens Park Rangers | | 0:3 * |
| |
Football League Cup 1973/74, Third round |
| 06.11.1973 | | York City | – | Orient | | 2:1 * |
| |
Football League Cup 1972/73, Second round |
| 05.09.1972 | | Wolverhampton Wanderers | – | Leyton Orient | | 2:1 |
| |
Football League Cup 1971/72, First Round |
| 25.08.1971 | | Notts County | – | Orient | | 3:1 * |
| |
Football League Cup 1970/71, First Round |
| 19.08.1970 | | Fulham | – | Orient | | 1:0 |
| |
Football League Cup 1969/70, First Round |
| 18.08.1969 | | Fulham | – | Leyton Orient | | 3:1 * |
| |
Football League Cup 1968/69, Third round |
| 24.09.1968 | | Orient | – | Crystal Palace | | 0:1 |
| |
Football League Cup 1967/68, First Round |
| 22.08.1967 | | Orient | – | Gillingham | | 1:3 |
| |
Football League Cup 1966/67, First Round |
| 24.08.1966 | | Brighton & Hove Albion | – | Leyton Orient | | 1:0 |
| |
Football League Cup 1965/66, Second round |
| 22.09.1965 | | Leyton Orient | – | Coventry City | | 0:3 |
| |
Football League Cup 1964/65, Third round |
| 14.10.1964 | | Charlton Athletic | – | Leyton Orient | | 2:1 |
| |
Football League Cup 1963/64, Second round |
| 25.09.1963 | | West Ham United | – | Leyton Orient | | 2:1 |
| London |
Football League Cup 1962/63, Fifth Round |
| 03.12.1962 | | Leyton Orient | – | Bury | | 0:2 |
| |
Football League Cup 1961/62, Second round |
| 30.10.1961 | | Blackpool | – | Leyton Orient | | 5:1 * |
| |
Football League Cup 1960/61, Second round |
| 14.11.1960 | | Leyton Orient | – | Chesterfield | | 0:1 |
| |
