FA Cup 2023/24, Second Round Proper |
 | 03.12.2023 | | Chesterfield | – | Leyton Orient | | 1:0 (1:0) |
| Chesterfield |
FA Cup 2022/23, First Round Proper |
| 05.11.2022 | | Crewe Alexandra | – | Leyton Orient | | 1:0 (0:0) |
| Crewe |
FA Cup 2021/22, Third Round Proper |
| 09.01.2022 | | Stoke City | – | Leyton Orient | | 2:0 (1:0) |
| Stoke-on-Trent |
FA Cup 2020/21, First Round Proper |
| 07.11.2020 | | Leyton Orient | – | Newport County | | 1:2 (1:1) * |
| London |
FA Cup 2019/20, First Round Proper |
| 10.11.2019 | | Leyton Orient | – | Maldon & Tiptree | | 1:2 (0:1) |
| London |
FA Cup 2018/19, Fourth Qualifying Round |
| 20.10.2018 | | Maidstone United | – | Leyton Orient | | 2:0 (0:0) |
| Maidstone |
FA Cup 2017/18, First Round Proper |
| 04.11.2017 | | Gillingham | – | Leyton Orient | | 2:1 (1:0) |
| Gillingham |
FA Cup 2016/17, First Round Proper |
| 06.11.2016 | | Sheffield United | – | Leyton Orient | | 6:0 (3:0) |
| Sheffield |
FA Cup 2015/16, Second Round Proper |
| 15.12.2015 | | Scunthorpe United | – | Leyton Orient | | 3:0 (0:0) * |
| Scunthorpe |
FA Cup 2014/15, First Round Proper |
| 08.11.2014 | | Oldham Athletic | – | Leyton Orient | | 1:0 (1:0) |
| Oldham |
FA Cup 2013/14, Third Round Proper |
| 04.01.2014 | | Yeovil Town | – | Leyton Orient | | 4:0 (1:0) |
| Yeovil |
FA Cup 2012/13, Third Round Proper |
| 15.01.2013 | | Leyton Orient | – | Hull City | | 1:2 aet
(0:1, 1:1) * |
| London |
FA Cup 2011/12, Second Round Proper |
| 03.12.2011 | | Leyton Orient | – | Gillingham | | 0:1 (0:1) |
| London |
FA Cup 2010/11, Fifth Round Proper |
| 02.03.2011 | | Arsenal | – | Leyton Orient | | 5:0 (3:0) * |
| London |
FA Cup 2009/10, First Round Proper |
| 17.11.2009 | | Leyton Orient | – | Tranmere Rovers | | 0:1 (0:0) * |
| London |
FA Cup 2008/09, Third Round Proper |
| 13.01.2009 | | Leyton Orient | – | Sheffield United | | 1:4 (1:0) |
| London |
FA Cup 2006/07, Second Round Proper |
| 12.12.2006 | | Leyton Orient | – | Torquay United | | 1:2 (0:0) * |
| London |
FA Cup 2005/06, Fourth Round Proper |
| 28.01.2006 | | Charlton Athletic | – | Leyton Orient | | 2:1 (1:0) |
| London |
FA Cup 2004/05, Second Round Proper |
| 04.12.2004 | | Oldham Athletic | – | Leyton Orient | | 4:0 (2:0) |
| Oldham |
FA Cup 2003/04, Second Round Proper |
| 06.12.2003 | | Cheltenham Town | – | Leyton Orient | | 3:1 (2:0) |
| Cheltenham |
FA Cup 2002/03, First Round Proper |
| 26.11.2002 | | Margate | – | Leyton Orient | | 1:0 (0:0) * |
| River |
FA Cup 2001/02, Fourth Round Proper |
| 26.01.2002 | | Everton | – | Leyton Orient | | 4:1 (3:1) |
| Liverpool |
FA Cup 2000/01, Third Round Proper |
| 06.01.2001 | | Leyton Orient | – | Tottenham Hotspur | | 0:1 (0:0) |
| London |
FA Cup 1999/00, First Round Proper |
| 09.11.1999 | | Cardiff City | – | Leyton Orient | | 3:1 (1:1) * |
| Cardiff |
FA Cup 1998/99, Fourth Round Proper |
| 23.01.1999 | | Bristol Rovers | – | Leyton Orient | | 3:0 (0:0) |
| Bristol |
FA Cup 1997/98, First Round Proper |
| 25.11.1997 | | Leyton Orient | – | Hendon | | 0:1 (0:0) * |
| London |
FA Cup 1996/97, Second Round Proper |
| 07.12.1996 | | Leyton Orient | – | Stevenage Borough | | 1:2 (1:2) |
| London |
FA Cup 1995/96, First Round Proper |
| 11.11.1995 | | Torquay United | – | Leyton Orient | | 1:0 (0:0) |
| Torquay |
FA Cup 1994/95, Second Round Proper |
| 03.12.1994 | | Leyton Orient | – | Bristol Rovers | | 0:2 (0:1) |
| London |
FA Cup 1992/93, Second Round Proper |
| 05.12.1992 | | Reading | – | Leyton Orient | | 3:0 (2:0) |
| Reading |
FA Cup 1991/92, Fourth Round Proper |
| 25.01.1992 | | Portsmouth | – | Leyton Orient | | 2:0 |
| Portsmouth |
FA Cup 1990/91, Third Round Proper |
| 21.01.1991 | | Swindon Town | – | Leyton Orient | | 1:0 * |
| Swindon |
FA Cup 1989/90, First Round Proper |
| 18.11.1989 | | Leyton Orient | – | Birmingham City | | 0:1 |
| London |
FA Cup 1988/89, First Round Proper |
| 28.11.1988 | | Leyton Orient | – | Enfield | | 0:1 (0:0) * |
| London |
FA Cup 1987/88, Fourth Round Proper |
| 30.01.1988 | | Leyton Orient | – | Nottingham Forest | | 1:2 (0:0) |
| London |
FA Cup 1986/87, Third Round Proper |
| 31.01.1987 | | West Ham United | – | Orient | | 4:1 (1:0) * |
| London |
FA Cup 1985/86, Fourth Round Proper |
| 25.01.1986 | | Sheffield Wednesday | – | Orient | | 5:0 |
| |
FA Cup 1984/85, Fourth Round Proper |
| 26.01.1985 | | Orient | – | Southampton | | 0:2 |
| |
FA Cup 1983/84, First Round Proper |
| 19.11.1983 | | Wimbledon | – | Orient | | 2:1 |
| |
FA Cup 1982/83, Second Round Proper |
| 11.12.1982 | | Newport County | – | Orient | | 1:0 |
| |
FA Cup 1981/82, Fifth Round Proper |
| 16.02.1982 | | Orient | – | Crystal Palace | | 0:1 * |
| |
FA Cup 1980/81, Third Round Proper |
| 03.01.1981 | | Orient | – | Luton Town | | 1:3 |
| |
FA Cup 1979/80, Fourth Round Proper |
| 26.01.1980 | | Orient | – | West Ham United | | 2:3 |
| London |
FA Cup 1978/79, Fourth Round Proper |
| 30.01.1979 | | Orient | – | Ipswich Town | | 0:2 * |
| |
FA Cup 1977/78, Semi Final |
| 08.04.1978 | | Arsenal | – | Orient | | 3:0 |
| London |
FA Cup 1976/77, Fourth Round Proper |
| 29.01.1977 | | Blackburn Rovers | – | Orient | | 3:0 |
| Blackburn |
FA Cup 1975/76, Third Round Proper |
| 03.01.1976 | | Orient | – | Cardiff City | | 0:1 |
| |
FA Cup 1974/75, Third Round Proper |
| 08.01.1975 | | Derby County | – | Orient | | 2:1 * |
| |
FA Cup 1973/74, Fourth Round Proper |
| 05.02.1974 | | Portsmouth | – | Orient | | 2:0 * |
| |
FA Cup 1972/73, Third Round Proper |
| 13.01.1973 | | Orient | – | Coventry City | | 1:4 |
| |
FA Cup 1971/72, Sixth Round Proper |
| 18.03.1972 | | Orient | – | Arsenal | | 0:1 (0:0) |
| London |
FA Cup 1970/71, Fourth Round Proper |
| 01.02.1971 | | Orient | – | Nottingham Forest | | 0:1 * |
| |
FA Cup 1969/70, First Round Proper |
| 17.11.1969 | | Orient | – | Walsall | | 0:2 (0:0) * |
| |
FA Cup 1968/69, First Round Proper |
| 20.11.1968 | | Gillingham | – | Orient | | 2:1 * |
| |
FA Cup 1967/68, Fourth Round Proper |
| 17.02.1968 | | Birmingham City | – | Orient | | 3:0 |
| |
FA Cup 1966/67, Second Round Proper |
| 10.01.1967 | | Brentford | – | Orient | | 3:1 * |
| |
FA Cup 1965/66, Third Round Proper |
| 22.01.1966 | | Leyton Orient | – | Norwich City | | 1:3 |
| |
FA Cup 1964/65, Third Round Proper |
| 09.01.1965 | | Southampton | – | Leyton Orient | | 3:1 |
| |
FA Cup 1963/64, Fourth Round Proper |
| 29.01.1964 | | West Ham United | – | Leyton Orient | | 3:0 * |
| London |
FA Cup 1962/63, Fifth Round Proper |
| 16.03.1963 | | Leyton Orient | – | Leicester City | | 0:1 |
| |
FA Cup 1961/62, Fourth Round Proper |
| 06.02.1962 | | Leyton Orient | – | Burnley | | 0:1 * |
| |
FA Cup 1960/61, Fifth Round Proper |
| 18.02.1961 | | Leyton Orient | – | Sheffield Wednesday | | 0:2 |
| |
FA Cup 1959/60, Third Round Proper |
| 09.01.1960 | | Liverpool | – | Leyton Orient | | 2:1 |
| |
FA Cup 1958/59, Third Round Proper |
| 10.01.1959 | | Blackburn Rovers | – | Leyton Orient | | 4:2 |
| |
FA Cup 1957/58, Fourth Round Proper |
| 25.01.1958 | | Cardiff City | – | Leyton Orient | | 4:1 |
| |
FA Cup 1956/57, Third Round Proper |
| 05.01.1957 | | Leyton Orient | – | Chelsea | | 0:2 |
| |
FA Cup 1955/56, Fourth Round Proper |
| 28.01.1956 | | Leyton Orient | – | Birmingham City | | 0:4 |
| |
FA Cup 1954/55, Second Round Proper |
| 11.12.1954 | | Leyton Orient | – | Workington | | 0:1 |
| |
FA Cup 1953/54, Sixth Round Proper |
| 13.03.1954 | | Leyton Orient | – | Port Vale | | 0:1 |
| |
FA Cup 1952/53, First Round Proper |
| 24.11.1952 | | Bristol Rovers | – | Leyton Orient | | 1:0 * |
| |
FA Cup 1951/52, Fifth Round Proper |
| 23.02.1952 | | Leyton Orient | – | Arsenal | | 0:3 |
| |
FA Cup 1950/51, First Round Proper |
| 25.11.1950 | | Leyton Orient | – | Ipswich Town | | 1:2 |
| |
FA Cup 1949/50, First Round Proper |
| 26.11.1949 | | Leyton Orient | – | Southend United | | 0:2 |
| |
FA Cup 1948/49, Second Round Proper |
| 11.12.1948 | | Darlington | – | Leyton Orient | | 1:0 |
| |
FA Cup 1947/48, First Round Proper |
| 29.11.1947 | | Gillingham | – | Leyton Orient | | 1:0 |
| |
FA Cup 1946/47, First Round Proper |
| 30.11.1946 | | Leyton Orient | – | Notts County | | 1:2 |
| |
FA Cup 1945/46, First Round Proper |
| 24.11.1945 | | Newport IOW | – | Leyton Orient | | 2:0 |
| |
FA Cup 1938/39, Second Round Proper |
| 10.12.1938 | | Walsall | – | Clapton Orient | | 4:2 |
| |
FA Cup 1937/38, Second Round Proper |
| 15.12.1937 | | York City | – | Clapton Orient | | 1:0 * |
| |
FA Cup 1936/37, Second Round Proper |
| 12.12.1936 | | Carlisle United | – | Clapton Orient | | 4:1 |
| |
FA Cup 1935/36, Fourth Round Proper |
| 25.01.1936 | | Middlesbrough | – | Clapton Orient | | 3:0 |
| |
FA Cup 1934/35, Second Round Proper |
| 08.12.1934 | | Clapton Orient | – | Chester | | 1:3 |
| |
FA Cup 1933/34, Third Round Proper |
| 13.01.1934 | | Grimsby Town | – | Clapton Orient | | 1:0 |
| |
FA Cup 1932/33, First Round Proper |
| 26.11.1932 | | Clapton Orient | – | Aldershot | | 0:1 |
| |
FA Cup 1931/32, Second Round Proper |
| 12.12.1931 | | Cardiff City | – | Clapton Orient | | 4:0 |
| |
FA Cup 1930/31, First Round Proper |
| 04.12.1930 | | Clapton Orient | – | Luton Town | | 2:4 * |
| |
FA Cup 1929/30, Fourth Round Proper |
| 25.01.1930 | | Newcastle United | – | Clapton Orient | | 3:1 |
| |
FA Cup 1928/29, Fourth Round Proper |
| 31.01.1929 | | Clapton Orient | – | Aston Villa | | 0:8 * |
| |
FA Cup 1927/28, Third Round Proper |
| 14.01.1928 | | Swindon Town | – | Clapton Orient | | 2:1 |
| |
FA Cup 1926/27, Third Round Proper |
| 12.01.1927 | | Port Vale | – | Clapton Orient | | 5:1 * |
| |
FA Cup 1925/26, Sixth Round Proper |
| 06.03.1926 | | Clapton Orient | – | Manchester City | | 1:6 |
| |
FA Cup 1924/25, First Round Proper |
| 10.01.1925 | | Nottingham Forest | – | Clapton Orient | | 1:0 |
| |
FA Cup 1923/24, First Round Proper |
| 21.01.1924 | | Swansea Town | – | Clapton Orient | | 2:1 * |
| |
FA Cup 1922/23, First Round Proper |
| 13.01.1923 | | Clapton Orient | – | Millwall | | 0:2 |
| |
FA Cup 1921/22, First Round Proper |
| 07.01.1922 | | Leicester City | – | Clapton Orient | | 2:0 |
| |
FA Cup 1920/21, First Round Proper |
| 08.01.1921 | | Bradford Park Avenue | – | Clapton Orient | | 1:0 |
| |
FA Cup 1919/20, First Round Proper |
| 10.01.1920 | | Manchester City | – | Clapton Orient | | 4:1 |
| |
FA Cup 1914/15, First Round Proper |
| 09.01.1915 | | Millwall | – | Clapton Orient | | 2:1 |
| |
FA Cup 1913/14, Second Round Proper |
| 31.01.1914 | | Brighton & Hove Albion | – | Clapton Orient | | 3:1 |
| |
FA Cup 1912/13, First Round Proper |
| 11.01.1913 | | Sunderland | – | Clapton Orient | | 6:0 |
| |
FA Cup 1911/12, First Round Proper |
| 13.01.1912 | | Clapton Orient | – | Everton | | 1:2 |
| |
FA Cup 1910/11, First Round Proper |
| 16.01.1911 | | Clapton Orient | – | Woolwich Arsenal | | 1:2 |
| |
FA Cup 1909/10, First Round Proper |
| 15.01.1910 | | West Bromwich Albion | – | Clapton Orient | | 2:0 |
| |
FA Cup 1908/09, First Round Proper |
| 16.01.1909 | | Newcastle United | – | Clapton Orient | | 5:0 |
| |
FA Cup 1905/06, First Round Proper |
| 17.01.1906 | | Chesterfield | – | Clapton Orient | | 3:0 * |
| |
