| Season | Competition |
Round Reached | Date |
Home | |
Away |
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| 2007/2008 | F.A. Cup | 1st Round Replay | Tue 27 Nov | Bristol Rvs. | 3 - 3 | Leyton Orient |
| after extra time, 90 minutes 2-2, Bristol Rovers won 6-5 on penalties |
| League Cup | 2nd Round | Tue 28 Aug | Cardiff City | 1 - 0 | Leyton Orient |
| (Associate Members) | Southern Section 2nd Round | Tue 09 Oct | Leyton Orient | 0 - 1 | Dag. & Red. |
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| 2006/2007 | F.A. Cup | 2nd Round Replay | Tue 12 Dec | Leyton Orient | 1 - 2 | Torquay Utd. |
| League Cup | 1st Round | Thu 24 Aug | Leyton Orient | 0 - 3 | West Brom. |
| (Associate Members) | Southern Section 2nd Round | Wed 01 Nov | Leyton Orient | 1 - 3 | Bristol City |
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| 2005/2006 | F.A. Cup | 4th Round | Sat 28 Jan | Charlton Ath. | 2 - 1 | Leyton Orient |
| League Cup | 1st Round | Tue 23 Aug | Leyton Orient | 1 - 3 | Luton Town |
| (Associate Members) | Southern Section 2nd Round | Wed 23 Nov | Oxford Utd. | 1 - 0 | Leyton Orient |
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| 2004/2005 | F.A. Cup | 2nd Round | Sat 04 Dec | Oldham Ath. | 4 - 0 | Leyton Orient |
| League Cup | 1st Round | Tue 24 Aug | Leyton Orient | 1 - 3 | Bournemouth |
| (Associate Members) | Southern Section Semi-Final | Tue 25 Jan | Leyton Orient | 1 - 2 | Bristol Rvs. |
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| 2003/2004 | F.A. Cup | 2nd Round | Sat 06 Dec | Cheltenham T. | 3 - 1 | Leyton Orient |
| League Cup | 1st Round | Tue 12 Aug | Cardiff City | 4 - 1 | Leyton Orient |
| (Associate Members) | Southern Section 1st Round | Wed 15 Oct | Dag. & Red. | 4 - 1 | Leyton Orient |
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| 2002/2003 | F.A. Cup | 1st Round Replay | Tue 26 Nov | Margate | 1 - 0 | Leyton Orient |
| League Cup | 2nd Round | Wed 02 Oct | Leyton Orient | 2 - 3 | Birmingham C. |
| (Associate Members) | Southern Section 2nd Round | Tue 12 Nov | Bournemouth | 1 - 0 | Leyton Orient |
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| 2001/2002 | F.A. Cup | 4th Round | Sat 26 Jan | Everton | 4 - 1 | Leyton Orient |
| League Cup | 1st Round | Tue 21 Aug | Leyton Orient | 2 - 4 | Crystal Palace |
| (Associate Members) | Southern Section 1st Round | Tue 16 Oct | Dag. & Red. | 3 - 2 | Leyton Orient |
| after extra time, 90 minutes 2-2, Dagenham & Redbridge won on the golden goal rule |
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| 2000/2001 | F.A. Cup | 3rd Round | Sat 06 Jan | Leyton Orient | 0 - 1 | Tottenham H. |
| League Cup | 2nd Round | Tue 26 Sep | Leyton Orient | 1 - 1 | Newcastle Utd. |
| (Associate Members) | Southern Section 2nd Round | Tue 09 Jan | Leyton Orient | 0 - 2 | Wycombe Wdrs. |
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| 1999/2000 | F.A. Cup | 1st Round Replay | Tue 09 Nov | Cardiff City | 3 - 1 | Leyton Orient |
| League Cup | 2nd Round | Tue 21 Sep | Leyton Orient | 1 - 0 | Grimsby Town |
| Grimsby Town won 4-2 on aggregate |
| (Associate Members) | Southern Section 1st Round | Wed 08 Dec | Reading | 1 - 0 | Leyton Orient |
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| 1998/1999 | F.A. Cup | 4th Round | Sat 23 Jan | Bristol Rvs. | 3 - 0 | Leyton Orient |
| League Cup | 2nd Round | Tue 22 Sep | Nottm. Forest | 0 - 0 | Leyton Orient |
| Nottingham Forest won 5-1 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 08 Dec | Peterborough | 3 - 0 | Leyton Orient |
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| 1997/1998 | F.A. Cup | 1st Round Replay | Tue 25 Nov | Leyton Orient | 0 - 1 | Hendon |
| League Cup | 2nd Round | Tue 30 Sep | Bolton Wdrs. | 4 - 4 | Leyton Orient |
| Bolton Wanderers won 7-5 on aggregate |
| (Associate Members) | Southern Section 2nd Round | Tue 06 Jan | Bournemouth | 2 - 0 | Leyton Orient |
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| 1996/1997 | F.A. Cup | 2nd Round | Sat 07 Dec | Leyton Orient | 1 - 2 | Stevenage B. |
| League Cup | 1st Round | Wed 04 Sep | Leyton Orient | 1 - 0 | Portsmouth |
| Portsmouth won 2-1 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 10 Dec | Luton Town | 2 - 1 | Leyton Orient |
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| 1995/1996 | F.A. Cup | 1st Round | Sat 11 Nov | Torquay Utd. | 1 - 0 | Leyton Orient |
| League Cup | 1st Round | Tue 22 Aug | Leyton Orient | 2 - 0 | Wycombe Wdrs. |
| Wycombe Wanderers won 3-2 on aggregate |
| (Associate Members) | Southern Section Preliminary Round Group One | Tue 07 Nov | Leyton Orient | 1 - 3 | Shrewsbury Tn. |
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| 1994/1995 | F.A. Cup | 2nd Round | Sat 03 Dec | Leyton Orient | 0 - 2 | Bristol Rvs. |
| League Cup | 1st Round | Tue 23 Aug | Leyton Orient | 1 - 1 | Barnet |
| Barnet won 5-1 on aggregate |
| (Associate Members) | Southern Section Final | Tue 14 Mar | Leyton Orient | 2 - 3 | Birmingham C. |
| Birmingham City won 4-2 on aggregate |
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| 1993/1994 | F.A. Cup | 2nd Round Replay | Tue 14 Dec | Exeter City | 2 - 2 | Leyton Orient |
| after extra time, 90 minutes 1-1, Exeter City won 5-4 on penalties |
| League Cup | 1st Round | Tue 24 Aug | Wycombe Wdrs. | 1 - 0 | Leyton Orient |
| Wycombe Wanderers won 3-0 on aggregate |
| (Associate Members) | Southern Section Semi-Final | Tue 08 Feb | Leyton Orient | 0 - 2 | Swansea City |
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| 1992/1993 | F.A. Cup | 2nd Round | Sat 05 Dec | Reading | 3 - 0 | Leyton Orient |
| League Cup | 1st Round | Wed 26 Aug | Millwall | 3 - 0 | Leyton Orient |
| Millwall won 5-2 on aggregate |
| (Associate Members) | Southern Section Quarter-Final | Tue 16 Feb | Swansea City | 1 - 0 | Leyton Orient |
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| 1991/1992 | F.A. Cup | 4th Round | Sat 25 Jan | Portsmouth | 2 - 0 | Leyton Orient |
| League Cup | 2nd Round | Wed 09 Oct | Sheff. Wed. | 4 - 1 | Leyton Orient |
| Sheffield Wednesday won 4-1 on aggregate |
| (Associate Members) | Southern Section Semi-Final | Tue 17 Mar | Leyton Orient | 0 - 1 | Stoke City |
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| 1990/1991 | F.A. Cup | 3rd Round Replay | Mon 21 Jan | Swindon Town | 1 - 0 | Leyton Orient |
| League Cup | 3rd Round Replay | Wed 07 Nov | Leyton Orient | 0 - 1 | Crystal Palace |
| (Associate Members) | Southern Section Preliminary Round Group Seven | Tue 29 Jan | Brentford | 2 - 0 | Leyton Orient |
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| 1989/1990 | F.A. Cup | 1st Round | Sat 18 Nov | Leyton Orient | 0 - 1 | Birmingham C. |
| League Cup | 2nd Round | Tue 03 Oct | Everton | 2 - 2 | Leyton Orient |
| Everton won 4-2 on aggregate |
| (Associate Members) | Southern Section Preliminary Round Group Play-offs | Tue 09 Jan | Mansfield Town | 2 - 1 | Leyton Orient |
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| 1988/1989 | F.A. Cup | 1st Round 2nd Replay | Mon 28 Nov | Leyton Orient | 0 - 1 | Enfield |
| League Cup | 3rd Round | Tue 01 Nov | Ipswich Town | 2 - 0 | Leyton Orient |
| (Associate Members) | Southern Section 1st Round | Tue 17 Jan | Colchester U. | 3 - 1 | Leyton Orient |
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| 1987/1988 | F.A. Cup | 4th Round | Sat 30 Jan | Leyton Orient | 1 - 2 | Nottm. Forest |
| League Cup | 1st Round | Tue 25 Aug | Millwall | 1 - 0 | Leyton Orient |
| Millwall won 2-1 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 19 Jan | Colchester U. | 1 - 1 | Leyton Orient |
| after extra time, 90 minutes 1-1, Colchester United won 4-3 on penalties |
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| 1986/1987 | F.A. Cup | 3rd Round Replay | Sat 31 Jan | West Ham Utd. | 4 - 1 | Orient* |
| League Cup | 1st Round | Tue 02 Sep | Cambridge U. | 1 - 0 | Orient* |
| Cambridge United won 3-2 on aggregate |
| (Associate Members) | Southern Section Preliminary Round Group Four | Mon 15 Dec | Orient* | 1 - 5 | Brentford |
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| 1985/1986 | F.A. Cup | 4th Round | Sat 25 Jan | Sheff. Wed. | 5 - 0 | Orient* |
| League Cup | 2nd Round | Wed 30 Oct | Tottenham H. | 4 - 0 | Orient* |
| Tottenham Hotspur won 4-2 on aggregate |
| (Associate Members) | Southern Section Quarter-Final | Mon 24 Mar | Orient* | 1 - 2 | Hereford Utd. |
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| 1984/1985 | F.A. Cup | 4th Round | Sat 26 Jan | Orient* | 0 - 2 | Southampton |
| League Cup | 2nd Round | Tue 09 Oct | Luton Town | 3 - 1 | Orient* |
| Luton Town won 7-2 on aggregate |
| (Associate Members) | Southern Section Semi-Final | Wed 08 May | Orient* | 1 - 1 | Newport Co. |
| after extra time, 90 minutes 1-1, Newport County won 4-2 on penalties |
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| 1983/1984 | F.A. Cup | 1st Round | Sat 19 Nov | Wimbledon | 2 - 1 | Orient* |
| League Cup | 1st Round | Tue 13 Sep | Orient* | 3 - 3 | Aldershot |
| Aldershot won 6-4 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 21 Feb | Brentford | 3 - 2 | Orient* |
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| 1982/1983 | F.A. Cup | 2nd Round | Sat 11 Dec | Newport Co. | 1 - 0 | Orient* |
| League Cup | 1st Round | Tue 14 Sep | Orient* | 2 - 0 | Gillingham |
| Gillingham won 3-2 on aggregate |
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| 1981/1982 | F.A. Cup | 5th Round Replay | Tue 16 Feb | Orient* | 0 - 1 | Crystal Palace |
| League Cup | 1st Round | Wed 16 Sep | Millwall | 3 - 2 | Orient* |
| Millwall won 4-3 on aggregate |
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| 1980/1981 | F.A. Cup | 3rd Round | Sat 03 Jan | Orient* | 1 - 3 | Luton Town |
| League Cup | 2nd Round | Wed 03 Sep | Tottenham H. | 3 - 1 | Orient* |
| Tottenham Hotspur won 4-1 on aggregate |
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| 1979/1980 | F.A. Cup | 4th Round | Sat 26 Jan | Orient* | 2 - 3 | West Ham Utd. |
| League Cup | 2nd Round | Tue 04 Sep | Wimbledon | 2 - 2 | Orient* |
| after extra time, aggregate 4-4, Wimbledon won 5-4 on penalties |
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| 1978/1979 | F.A. Cup | 4th Round Replay | Tue 30 Jan | Orient* | 0 - 2 | Ipswich Town |
| League Cup | 2nd Round | Tue 29 Aug | Orient* | 1 - 2 | Chesterfield |
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| 1977/1978 | F.A. Cup | Semi Final | Sat 08 Apr | Arsenal | 3 - 0 | Orient* |
| played at Stamford Bridge |
| League Cup | 2nd Round | Wed 31 Aug | Derby County | 3 - 1 | Orient* |
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| 1976/1977 | F.A. Cup | 4th Round | Sat 29 Jan | Blackburn R. | 3 - 0 | Orient* |
| League Cup | 3rd Round 2nd Replay | Tue 19 Oct | Millwall | 3 - 0 | Orient* |
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| 1975/1976 | F.A. Cup | 3rd Round | Sat 03 Jan | Orient* | 0 - 1 | Cardiff City |
| League Cup | 2nd Round | Tue 09 Sep | Birmingham C. | 4 - 0 | Orient* |
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| 1974/1975 | F.A. Cup | 3rd Round Replay | Wed 08 Jan | Derby County | 2 - 1 | Orient* |
| League Cup | 2nd Round Replay | Tue 17 Sep | Orient* | 0 - 3 | Q.P.R. |
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| 1973/1974 | F.A. Cup | 4th Round 2nd Replay | Tue 05 Feb | Portsmouth | 2 - 0 | Orient* |
| played at neutral ground |
| League Cup | 3rd Round Replay | Tue 06 Nov | York City | 2 - 1 | Orient* |
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| 1972/1973 | F.A. Cup | 3rd Round | Sat 13 Jan | Orient* | 1 - 4 | Coventry City |
| League Cup | 2nd Round | Tue 05 Sep | Wolves | 2 - 1 | Orient* |
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| 1971/1972 | F.A. Cup | 6th Round | Sat 18 Mar | Orient* | 0 - 1 | Arsenal |
| League Cup | 1st Round Replay | Wed 25 Aug | Notts. County | 3 - 1 | Orient* |
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| 1970/1971 | F.A. Cup | 4th Round Replay | Mon 01 Feb | Orient* | 0 - 1 | Nottm. Forest |
| League Cup | 1st Round | Wed 19 Aug | Fulham | 1 - 0 | Orient* |
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| 1969/1970 | F.A. Cup | 1st Round Replay | Mon 17 Nov | Orient* | 0 - 2 | Walsall |
| League Cup | 1st Round Replay | Mon 18 Aug | Fulham | 3 - 1 | Orient* |
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| 1968/1969 | F.A. Cup | 1st Round Replay | Wed 20 Nov | Gillingham | 2 - 0 | Orient* |
| League Cup | 3rd Round | Tue 24 Sep | Orient* | 0 - 1 | Crystal Palace |
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| 1967/1968 | F.A. Cup | 4th Round | Sat 17 Feb | Birmingham C. | 3 - 0 | Orient* |
| League Cup | 1st Round | Tue 22 Aug | Orient* | 1 - 3 | Gillingham |
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| 1966/1967 | F.A. Cup | 2nd Round Replay | Tue 10 Jan | Brentford | 3 - 1 | Orient* |
| League Cup | 1st Round | Wed 24 Aug | Brighton & HA | 1 - 0 | Orient* |
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| 1965/1966 | F.A. Cup | 3rd Round | Sat 22 Jan | Leyton Orient | 1 - 3 | Norwich City |
| League Cup | 2nd Round | Wed 22 Sep | Leyton Orient | 0 - 3 | Coventry City |
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| 1964/1965 | F.A. Cup | 3rd Round | Sat 09 Jan | Southampton | 3 - 1 | Leyton Orient |
| League Cup | 3rd Round | Wed 14 Oct | Charlton Ath. | 2 - 1 | Leyton Orient |
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| 1963/1964 | F.A. Cup | 4th Round Replay | Wed 29 Jan | West Ham Utd. | 3 - 0 | Leyton Orient |
| League Cup | 2nd Round | Wed 25 Sep | West Ham Utd. | 2 - 1 | Leyton Orient |
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| 1962/1963 | F.A. Cup | 5th Round | Sat 16 Mar | Leyton Orient | 0 - 1 | Leicester City |
| League Cup | Quarter Final | Mon 03 Dec | Leyton Orient | 0 - 2 | Bury |
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| 1961/1962 | F.A. Cup | 4th Round Replay | Tue 06 Feb | Leyton Orient | 0 - 1 | Burnley |
| League Cup | 2nd Round Replay | Mon 30 Oct | Blackpool | 5 - 1 | Leyton Orient |
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| 1960/1961 | F.A. Cup | 5th Round | Sat 18 Feb | Leyton Orient | 0 - 2 | Sheff. Wed. |
| League Cup | 2nd Round | Mon 14 Nov | Leyton Orient | 0 - 1 | Chesterfield |
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| 1959/1960 | F.A. Cup | 3rd Round | Sat 09 Jan | Liverpool | 2 - 1 | Leyton Orient |
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| 1958/1959 | F.A. Cup | 3rd Round | Sat 10 Jan | Blackburn R. | 4 - 2 | Leyton Orient |
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| 1957/1958 | F.A. Cup | 4th Round | Sat 25 Jan | Cardiff City | 4 - 1 | Leyton Orient |
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| 1956/1957 | F.A. Cup | 3rd Round | Sat 05 Jan | Leyton Orient | 0 - 2 | Chelsea |
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| 1955/1956 | F.A. Cup | 4th Round | Sat 28 Jan | Leyton Orient | 0 - 4 | Birmingham C. |
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| 1954/1955 | F.A. Cup | 2nd Round | Sat 11 Dec | Leyton Orient | 0 - 1 | Workington |
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| 1953/1954 | F.A. Cup | 6th Round | Sat 13 Mar | Leyton Orient | 0 - 1 | Port Vale |
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| 1952/1953 | F.A. Cup | 1st Round Replay | Mon 24 Nov | Bristol Rvs. | 1 - 0 | Leyton Orient |
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| 1951/1952 | F.A. Cup | 5th Round | Sat 23 Feb | Leyton Orient | 0 - 3 | Arsenal |
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| 1950/1951 | F.A. Cup | 1st Round | Sat 25 Nov | Leyton Orient | 1 - 2 | Ipswich Town |
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| 1949/1950 | F.A. Cup | 1st Round | Sat 26 Nov | Leyton Orient | 0 - 2 | Southend Utd. |
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| 1948/1949 | F.A. Cup | 2nd Round | Sat 11 Dec | Darlington | 1 - 0 | Leyton Orient |
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| 1947/1948 | F.A. Cup | 1st Round | Sat 29 Nov | Gillingham | 1 - 0 | Leyton Orient |
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| 1946/1947 | F.A. Cup | 1st Round | Sat 30 Nov | Leyton Orient | 1 - 2 | Notts. County |
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| 1945/1946 | F.A. Cup | 1st Round | Sat 24 Nov | Newport IoW | 2 - 0 | Clapton Orient* |
| Newport I.o.W. won 3-2 on aggregate |
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| 1938/1939 | F.A. Cup | 2nd Round | Sat 10 Dec | Walsall | 4 - 2 | Clapton Orient* |
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| 1937/1938 | F.A. Cup | 2nd Round Replay | Wed 15 Dec | York City | 1 - 0 | Clapton Orient* |
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| 1936/1937 | F.A. Cup | 2nd Round | Sat 12 Dec | Carlisle Utd. | 4 - 1 | Clapton Orient* |
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| 1935/1936 | F.A. Cup | 4th Round | Sat 25 Jan | Middlesbrough | 3 - 0 | Clapton Orient* |
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| 1934/1935 | F.A. Cup | 2nd Round | Sat 08 Dec | Clapton Orient* | 1 - 3 | Chester |
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| 1933/1934 | F.A. Cup | 3rd Round | Sat 13 Jan | Grimsby Town | 1 - 0 | Clapton Orient* |
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| 1932/1933 | F.A. Cup | 1st Round | Sat 26 Nov | Clapton Orient* | 0 - 1 | Aldershot |
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| 1931/1932 | F.A. Cup | 2nd Round | Sat 12 Dec | Cardiff City | 4 - 0 | Clapton Orient* |
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| 1930/1931 | F.A. Cup | 1st Round Replay | Thu 04 Dec | Clapton Orient* | 2 - 4 | Luton Town |
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| 1929/1930 | F.A. Cup | 4th Round | Sat 25 Jan | Newcastle Utd. | 3 - 1 | Clapton Orient* |
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| 1928/1929 | F.A. Cup | 4th Round Replay | Thu 31 Jan | Clapton Orient* | 0 - 8 | Aston Villa |
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| 1927/1928 | F.A. Cup | 3rd Round | Sat 14 Jan | Swindon Town | 2 - 1 | Clapton Orient* |
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| 1926/1927 | F.A. Cup | 3rd Round Replay | Wed 12 Jan | Port Vale | 5 - 1 | Clapton Orient* |
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| 1925/1926 | F.A. Cup | 6th Round | Sat 06 Mar | Clapton Orient* | 1 - 6 | Man. City |
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| 1924/1925 | F.A. Cup | 1st Round | Sat 10 Jan | Nottm. Forest | 1 - 0 | Clapton Orient* |
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| 1923/1924 | F.A. Cup | 1st Round 2nd Replay | Mon 21 Jan | Swansea Town | 2 - 1 | Clapton Orient* |
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| 1922/1923 | F.A. Cup | 1st Round | Sat 13 Jan | Clapton Orient* | 0 - 2 | Millwall |
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| 1921/1922 | F.A. Cup | 1st Round | Sat 07 Jan | Leicester City | 2 - 0 | Clapton Orient* |
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| 1920/1921 | F.A. Cup | 1st Round | Sat 08 Jan | Bradford P.A. | 1 - 0 | Clapton Orient* |
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| 1919/1920 | F.A. Cup | 1st Round | Sat 10 Jan | Man. City | 4 - 1 | Clapton Orient* |
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| 1914/1915 | F.A. Cup | 1st Round | Sat 09 Jan | Millwall | 2 - 1 | Clapton Orient* |
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| 1913/1914 | F.A. Cup | 2nd Round | Sat 31 Jan | Brighton & HA | 3 - 1 | Clapton Orient* |
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| 1912/1913 | F.A. Cup | 1st Round | Sat 11 Jan | Sunderland | 6 - 0 | Clapton Orient* |
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| 1911/1912 | F.A. Cup | 1st Round | Sat 13 Jan | Clapton Orient* | 1 - 2 | Everton |
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| 1910/1911 | F.A. Cup | 1st Round | Mon 16 Jan | Clapton Orient* | 1 - 2 | Woolwich Arsenal |
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| 1909/1910 | F.A. Cup | 1st Round | Sat 15 Jan | West Brom. | 2 - 0 | Clapton Orient* |
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| 1908/1909 | F.A. Cup | 1st Round | Sat 16 Jan | Newcastle Utd. | 5 - 0 | Clapton Orient* |
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| 1905/1906 | |
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