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 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 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, 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, Second round |
| 26.09.2000 | | Leyton Orient | – | Newcastle United | | 1:1 (1:1) |
| London |
Football League Cup 2000/01, First Round |
| 22.08.2000 | | Leyton Orient | – | Reading | | 1:1 (0:1) |
| London |
Football League Cup 1999/00, First Round |
| 24.08.1999 | | Leyton Orient | – | Swindon Town | | 1:1 (0:0) |
| London |
Football League Cup 1998/99, Second round |
| 22.09.1998 | | Nottingham Forest | – | Leyton Orient | | 0:0 |
| Nottingham |
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, First Round |
| 13.08.1997 | | Brighton & Hove Albion | – | Leyton Orient | | 1:1 (0:1) |
| Hove |
Football League Cup 1994/95, First Round |
| 23.08.1994 | | Leyton Orient | – | Barnet | | 1:1 (0:1) |
| 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 |
| 24.09.1991 | | Leyton Orient | – | Sheffield Wednesday | | 0:0 |
| 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 |
| 26.09.1990 | | Charlton Athletic | – | Leyton Orient | | 2:2 |
| 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 1988/89, First Round |
| 06.09.1988 | | Aldershot | – | Leyton Orient | | 0:0 |
| Aldershot |
Football League Cup 1987/88, First Round |
| 18.08.1987 | | Leyton Orient | – | Millwall | | 1:1 |
| London |
Football League Cup 1986/87, First Round |
| 26.08.1986 | | Orient | – | Cambridge United | | 2:2 |
| London |
Football League Cup 1985/86, First Round |
| 03.09.1985 | | Leyton Orient | – | Aldershot | | 2:2 |
| |
Football League Cup 1984/85, First Round |
| 05.09.1984 | | Southend United | – | Leyton Orient | | 0:0 |
| |
Football League Cup 1983/84, First Round |
| 13.09.1983 | | Leyton Orient | – | Aldershot | | 3:3 |
| |
Football League Cup 1981/82, First Round |
| 01.09.1981 | | Leyton Orient | – | Millwall | | 1:1 |
| |
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 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 1974/75, Second round |
| 10.09.1974 | | Queens Park Rangers | – | Orient | | 1:1 |
| |
Football League Cup 1973/74, Third round |
| 31.10.1973 | | Orient | – | York City | | 1:1 |
| |
Football League Cup 1971/72, First Round |
| 17.08.1971 | | Orient | – | Notts County | | 1:1 |
| |
Football League Cup 1969/70, First Round |
| 13.08.1969 | | Leyton Orient | – | Fulham | | 0:0 |
| |
Football League Cup 1968/69, First Round |
| 14.08.1968 | | Gillingham | – | Orient | | 2:2 |
| |
Football League Cup 1962/63, Second round |
| 26.09.1962 | | Newcastle United | – | Leyton Orient | | 1:1 |
| |
Football League Cup 1961/62, Second round |
| 04.10.1961 | | Leyton Orient | – | Blackpool | | 1:1 |
| |
Football League Cup 1960/61, First Round |
| 12.10.1960 | | Chester City | – | Leyton Orient | | 2:2 |
| |
