Football League Cup 2024/25, Third Round |
| 17.09.2024 | | Brentford | | Leyton Orient | | 3:1 (3:1) |
| Brentford |
Football League Cup 2024/25, Second Round |
| 27.08.2024 | | Millwall | | Leyton Orient | | 0:1 (0:1) |
| London |
Football League Cup 2024/25, First Round |
| 13.08.2024 | | Leyton Orient | | Newport County | | 4:1 (2:0) |
| London |
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 2021/22, First Round |
| 11.08.2021 | | Leyton Orient | | Queens Park Rangers | | 1:1 (0:1), pen. 3:5 |
| London |
Football League Cup 2020/21, Third round |
| 22.09.2020 | | Leyton Orient | | Tottenham Hotspur | | -:+ |
| London |
Football League Cup 2020/21, Second round |
| 15.09.2020 | | Leyton Orient | | Plymouth Argyle | | 3:2 (0:2) * |
| London |
Football League Cup 2020/21, First Round |
| 05.09.2020 | | Forest Green Rovers | | Leyton Orient | | 1:2 (1:0) * |
| Nailsworth |
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 2014/15, Second round |
| 27.08.2014 | | Aston Villa | | Leyton Orient | | 0:1 (0:0) |
| Birmingham |
Football League Cup 2014/15, First Round |
| 12.08.2014 | | Plymouth Argyle | | Leyton Orient | | 3:3 aet (1:2, 2:2), pen. 5:6 |
| Plymouth |
Football League Cup 2013/14, Second round |
| 27.08.2013 | | Leyton Orient | | Hull City | | 0:1 aet (0:0) |
| London |
Football League Cup 2013/14, First Round |
| 06.08.2013 | | Leyton Orient | | Coventry City | | 3:2 (2:1) |
| London |
Football League Cup 2012/13, Second round |
| 29.08.2012 | | Everton | | Leyton Orient | | 5:0 (4:0) |
| Liverpool |
Football League Cup 2012/13, First Round |
| 14.08.2012 | | Charlton Athletic | | Leyton Orient | | 1:1 aet (1:1, 1:1), pen. 3:4 |
| London |
Football League Cup 2011/12, Third round |
| 20.09.2011 | | Blackburn Rovers | | Leyton Orient | | 3:2 (1:0) |
| Blackburn |
Football League Cup 2011/12, Second round |
| 30.08.2011 | | Leyton Orient | | Bristol Rovers | | 3:2 (2:0) |
| London |
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 | | Leyton Orient | | West Bromwich Albion | | 0:2 (0:1) |
| London |
Football League Cup 2010/11, First Round |
| 10.08.2010 | | Swindon Town | | Leyton Orient | | 1:2 (1:0) |
| Swindon |
Football League Cup 2009/10, Second round |
| 26.08.2009 | | Leyton Orient | | Stoke City | | 0:1 aet (0:0) |
| London |
Football League Cup 2009/10, First Round |
| 11.08.2009 | | Colchester United | | Leyton Orient | | 1:2 (0:1) |
| Colchester |
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 2007/08, First Round |
| 14.08.2007 | | Queens Park Rangers | | Leyton Orient | | 1:2 (0:0) |
| London |
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 2002/03, First Round |
| 10.09.2002 | | Leyton Orient | | Queens Park Rangers | | 3:2 (2:0) |
| 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 |
| 26.09.2000 | | Leyton Orient | | Newcastle United | | 1:1 (1:1) |
| 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 2000/01, First Round |
| 05.09.2000 | | Reading | | Leyton Orient | | 0:2 (0:0) |
| Reading |
Football League Cup 2000/01, First Round |
| 22.08.2000 | | Leyton Orient | | Reading | | 1:1 (0:1) |
| London |
Football League Cup 1999/00, Second round |
| 21.09.1999 | | Leyton Orient | | Grimsby Town | | 1:0 (1:0) |
| London |
Football League Cup 1999/00, Second round |
| 14.09.1999 | | Grimsby Town | | Leyton Orient | | 4:1 (2:1) |
| Cleethorpes |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Leyton Orient | | Swindon Town | | 1:1 (0:0) |
| London |
Football League Cup 1999/00, First Round |
| 10.08.1999 | | Swindon Town | | Leyton Orient | | 0:1 (0:0) |
| Swindon |
Football League Cup 1998/99, Second round |
| 22.09.1998 | | Nottingham Forest | | Leyton Orient | | 0:0 |
| Nottingham |
Football League Cup 1998/99, Second round |
| 15.09.1998 | | Leyton Orient | | Nottingham Forest | | 1:5 (0:4) |
| London |
Football League Cup 1998/99, First Round |
| 18.08.1998 | | Bristol Rovers | | Leyton Orient | | 1:2 aet (1:1, 1:1) |
| Bristol |
Football League Cup 1998/99, First Round |
| 11.08.1998 | | Leyton Orient | | Bristol Rovers | | 1:1 (1:0) |
| London |
Football League Cup 1997/98, Second round |
| 30.09.1997 | | Bolton Wanderers | | Leyton Orient | | 4:4 (2:2) |
| Bolton |
Football League Cup 1997/98, Second round |
| 16.09.1997 | | Leyton Orient | | Bolton Wanderers | | 1:3 (1:2) |
| London |
Football League Cup 1997/98, First Round |
| 26.08.1997 | | Leyton Orient | | Brighton & Hove Albion | | 3:1 (1:1) |
| London |
Football League Cup 1997/98, First Round |
| 13.08.1997 | | Brighton & Hove Albion | | Leyton Orient | | 1:1 (0:1) |
| Hove |
Football League Cup 1996/97, First Round |
| 04.09.1996 | | Leyton Orient | | Portsmouth | | 1:0 (0:0) |
| 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 |
| 22.08.1995 | | Leyton Orient | | Wycombe Wanderers | | 2:0 (1:0) |
| London |
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 |
| 23.08.1994 | | Leyton Orient | | Barnet | | 1:1 (0:1) |
| London |
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 1992/93, First Round |
| 18.08.1992 | | Leyton Orient | | Millwall | | 2:2 (1:0) |
| 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, Second round |
| 24.09.1991 | | Leyton Orient | | Sheffield Wednesday | | 0:0 |
| London |
Football League Cup 1991/92, First Round |
| 10.09.1991 | | Northampton Town | | Leyton Orient | | 2:0 (1:0) |
| Northampton |
Football League Cup 1991/92, First Round |
| 20.08.1991 | | Leyton Orient | | Northampton Town | | 5:0 (3:0) |
| London |
Football League Cup 1990/91, Third round |
| 07.11.1990 | | Leyton Orient | | Crystal Palace | | 0:1 * |
| London |
Football League Cup 1990/91, Third round |
| 30.10.1990 | | Crystal Palace | | Leyton Orient | | 0:0 |
| London |
Football League Cup 1990/91, Second round |
| 09.10.1990 | | Leyton Orient | | Charlton Athletic | | 1:0 |
| London |
Football League Cup 1990/91, Second round |
| 26.09.1990 | | Charlton Athletic | | Leyton Orient | | 2:2 |
| London |
Football League Cup 1990/91, First Round |
| 04.09.1990 | | Leyton Orient | | Maidstone United | | 4:1 |
| London |
Football League Cup 1990/91, First Round |
| 29.08.1990 | | Maidstone United | | Leyton Orient | | 2:2 |
| Dartford |
Football League Cup 1989/90, Second round |
| 03.10.1989 | | Everton | | Leyton Orient | | 2:2 |
| Liverpool |
Football League Cup 1989/90, Second round |
| 19.09.1989 | | Leyton Orient | | Everton | | 0:2 |
| London |
Football League Cup 1989/90, First Round |
| 29.08.1989 | | Leyton Orient | | Gillingham | | 3:0 |
| London |
Football League Cup 1989/90, First Round |
| 22.08.1989 | | Gillingham | | Leyton Orient | | 1:4 |
| Gillingham |
Football League Cup 1988/89, Third round |
| 01.11.1988 | | Ipswich Town | | Leyton Orient | | 2:0 |
| Ipswich |
Football League Cup 1988/89, Second round |
| 11.10.1988 | | Stoke City | | Leyton Orient | | 1:2 aet (1:2), pen. 2:3 |
| Stoke-on-Trent |
Football League Cup 1988/89, Second round |
| 27.09.1988 | | Leyton Orient | | Stoke City | | 1:2 |
| London |
Football League Cup 1988/89, First Round |
| 06.09.1988 | | Aldershot | | Leyton Orient | | 0:0 |
| Aldershot |
Football League Cup 1988/89, First Round |
| 30.08.1988 | | Leyton Orient | | Aldershot | | 2:0 |
| London |
Football League Cup 1987/88, First Round |
| 25.08.1987 | | Millwall | | Leyton Orient | | 1:0 |
| London |
Football League Cup 1987/88, First Round |
| 18.08.1987 | | Leyton Orient | | Millwall | | 1:1 |
| London |
Football League Cup 1986/87, First Round |
| 02.09.1986 | | Cambridge United | | Orient | | 1:0 |
| Cambridge |
Football League Cup 1986/87, First Round |
| 26.08.1986 | | Orient | | Cambridge United | | 2:2 |
| London |
Football League Cup 1985/86, Second round |
| 30.10.1985 | | Tottenham Hotspur | | Leyton Orient | | 4:0 |
| London |
Football League Cup 1985/86, Second round |
| 23.09.1985 | | Leyton Orient | | Tottenham Hotspur | | 2:0 |
| |
Football League Cup 1985/86, First Round |
| 03.09.1985 | | Leyton Orient | | Aldershot | | 2:2 |
| |
Football League Cup 1985/86, First Round |
| 20.08.1985 | | Aldershot | | Leyton Orient | | 1:3 |
| |
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 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 | | Leyton Orient | | Aldershot | | 3:3 |
| |
Football League Cup 1983/84, First Round |
| 30.08.1983 | | Aldershot | | Leyton Orient | | 3:1 |
| |
Football League Cup 1982/83, First Round |
| 14.09.1982 | | Leyton Orient | | Gillingham | | 2:0 |
| |
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 1981/82, First Round |
| 01.09.1981 | | Leyton Orient | | Millwall | | 1:1 |
| |
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 1979/80, Second round |
| 04.09.1979 | | Wimbledon | | Orient | | 2:2 aet, pen. 5:4 |
| |
Football League Cup 1979/80, Second round |
| 29.08.1979 | | Orient | | Wimbledon | | 2:2 |
| |
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 1977/78, First Round |
| 13.08.1977 | | Fulham | | Leyton Orient | | 0:2 |
| |
Football League Cup 1976/77, Third round |
| 19.10.1976 | | Millwall | | Orient | | 3:0 * |
| |
Football League Cup 1976/77, Third round |
| 12.10.1976 | | Orient | | Millwall | | 0:0 aet * |
| |
Football League Cup 1976/77, Third round |
| 21.09.1976 | | Millwall | | Orient | | 0:0 |
| |
Football League Cup 1976/77, Second round |
| 31.08.1976 | | Orient | | Hull City | | 1:0 |
| |
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 1974/75, Second round |
| 10.09.1974 | | Queens Park Rangers | | Orient | | 1:1 |
| |
Football League Cup 1973/74, Third round |
| 06.11.1973 | | York City | | Orient | | 2:1 * |
| |
Football League Cup 1973/74, Third round |
| 31.10.1973 | | Orient | | York City | | 1:1 |
| |
Football League Cup 1973/74, Second round |
| 09.10.1973 | | Orient | | Blackburn Rovers | | 2:0 |
| |
Football League Cup 1973/74, First Round |
| 28.08.1973 | | Brentford | | Orient | | 1:2 |
| |
Football League Cup 1972/73, Second round |
| 05.09.1972 | | Wolverhampton Wanderers | | Leyton Orient | | 2:1 |
| |
Football League Cup 1972/73, First Round |
| 16.08.1972 | | Leyton Orient | | Watford | | 2:0 |
| |
Football League Cup 1971/72, First Round |
| 25.08.1971 | | Notts County | | Orient | | 3:1 * |
| |
Football League Cup 1971/72, First Round |
| 17.08.1971 | | Orient | | Notts County | | 1:1 |
| |
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 1969/70, First Round |
| 13.08.1969 | | Leyton Orient | | Fulham | | 0:0 |
| |
Football League Cup 1968/69, Third round |
| 24.09.1968 | | Orient | | Crystal Palace | | 0:1 |
| |
Football League Cup 1968/69, Second round |
| 03.09.1968 | | Orient | | Fulham | | 1:0 |
| |
Football League Cup 1968/69, First Round |
| 20.08.1968 | | Orient | | Gillingham | | 3:0 * |
| |
Football League Cup 1968/69, First Round |
| 14.08.1968 | | Gillingham | | Orient | | 2:2 |
| |
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 1964/65, Second round |
| 23.09.1964 | | Leyton Orient | | Barnsley | | 3:0 |
| |
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 1962/63, Fourth Round |
| 12.11.1962 | | Leyton Orient | | Charlton Athletic | | 3:2 |
| |
Football League Cup 1962/63, Third round |
| 17.10.1962 | | Leyton Orient | | Chester | | 9:2 |
| |
Football League Cup 1962/63, Second round |
| 01.10.1962 | | Leyton Orient | | Newcastle United | | 4:2 * |
| |
Football League Cup 1962/63, Second round |
| 26.09.1962 | | Newcastle United | | Leyton Orient | | 1:1 |
| |
Football League Cup 1961/62, Second round |
| 30.10.1961 | | Blackpool | | Leyton Orient | | 5:1 * |
| |
Football League Cup 1961/62, Second round |
| 04.10.1961 | | Leyton Orient | | Blackpool | | 1:1 |
| |
Football League Cup 1961/62, First Round |
| 11.09.1961 | | Stockport County | | Leyton Orient | | 0:1 |
| |
Football League Cup 1960/61, Second round |
| 14.11.1960 | | Leyton Orient | | Chesterfield | | 0:1 |
| |
Football League Cup 1960/61, First Round |
| 17.10.1960 | | Leyton Orient | | Chester | | 1:0 * |
| |
Football League Cup 1960/61, First Round |
| 12.10.1960 | | Chester City | | Leyton Orient | | 2:2 |
| |