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 2014/15, Second round |
| 27.08.2014 | | Aston Villa | – | Leyton Orient | | 0:1 (0:0) |
| Birmingham |
Football League Cup 2013/14, First Round |
| 06.08.2013 | | Leyton Orient | – | Coventry City | | 3:2 (2:1) |
| London |
Football League Cup 2011/12, Second round |
| 30.08.2011 | | Leyton Orient | – | Bristol Rovers | | 3:2 (2:0) |
| 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, First Round |
| 11.08.2009 | | Colchester United | – | Leyton Orient | | 1:2 (0:1) |
| Colchester |
Football League Cup 2007/08, First Round |
| 14.08.2007 | | Queens Park Rangers | – | Leyton Orient | | 1:2 (0:0) |
| London |
Football League Cup 2002/03, First Round |
| 10.09.2002 | | Leyton Orient | – | Queens Park Rangers | | 3:2 (2:0) |
| London |
Football League Cup 2000/01, First Round |
| 05.09.2000 | | Reading | – | Leyton Orient | | 0:2 (0:0) |
| Reading |
Football League Cup 1999/00, Second round |
| 21.09.1999 | | Leyton Orient | – | Grimsby Town | | 1:0 (1:0) |
| 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, First Round |
| 18.08.1998 | | Bristol Rovers | – | Leyton Orient | | 1:2 aet
(1:1, 1:1) |
| Bristol |
Football League Cup 1997/98, First Round |
| 26.08.1997 | | Leyton Orient | – | Brighton & Hove Albion | | 3:1 (1:1) |
| London |
Football League Cup 1996/97, First Round |
| 04.09.1996 | | Leyton Orient | – | Portsmouth | | 1:0 (0:0) |
| London |
Football League Cup 1995/96, First Round |
| 22.08.1995 | | Leyton Orient | – | Wycombe Wanderers | | 2:0 (1:0) |
| London |
Football League Cup 1991/92, First Round |
| 20.08.1991 | | Leyton Orient | – | Northampton Town | | 5:0 (3:0) |
| London |
Football League Cup 1990/91, Second round |
| 09.10.1990 | | Leyton Orient | – | Charlton Athletic | | 1:0 |
| London |
Football League Cup 1990/91, First Round |
| 04.09.1990 | | Leyton Orient | – | Maidstone United | | 4:1 |
| 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, 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, First Round |
| 30.08.1988 | | Leyton Orient | – | Aldershot | | 2:0 |
| London |
Football League Cup 1985/86, Second round |
| 23.09.1985 | | Leyton Orient | – | Tottenham Hotspur | | 2:0 |
| |
Football League Cup 1985/86, First Round |
| 20.08.1985 | | Aldershot | – | Leyton Orient | | 1:3 |
| |
Football League Cup 1984/85, First Round |
| 28.08.1984 | | Leyton Orient | – | Southend United | | 2:1 |
| |
Football League Cup 1982/83, First Round |
| 14.09.1982 | | Leyton Orient | – | Gillingham | | 2:0 |
| |
Football League Cup 1977/78, First Round |
| 13.08.1977 | | Fulham | – | Leyton Orient | | 0:2 |
| |
Football League Cup 1976/77, Second round |
| 31.08.1976 | | Orient | – | Hull City | | 1:0 |
| |
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, First Round |
| 16.08.1972 | | Leyton Orient | – | Watford | | 2:0 |
| |
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 1964/65, Second round |
| 23.09.1964 | | Leyton Orient | – | Barnsley | | 3:0 |
| |
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 1961/62, First Round |
| 11.09.1961 | | Stockport County | – | Leyton Orient | | 0:1 |
| |
Football League Cup 1960/61, First Round |
| 17.10.1960 | | Leyton Orient | – | Chester | | 1:0 * |
| |
