| Season | Competition |
Round Reached | Date |
Home | |
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| 2007/2008 | F.A. Cup | 4th Round | Fri 25 Jan | Southend Utd. | 0 - 1 | Barnsley |
| League Cup | 3rd Round | Tue 25 Sep | Blackpool | 2 - 1 | Southend Utd. |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Southern Section 1st Round | Tue 04 Sep | Southend Utd. | 2 - 2 | Dag. & Red. |
| after extra time, 90 minutes 2-2, Dagenham & Redbridge won 7-6 on penalties |
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| 2006/2007 | F.A. Cup | 4th Round | Sat 27 Jan | Tottenham H. | 3 - 1 | Southend Utd. |
| League Cup | Quarter Final | Wed 20 Dec | Tottenham H. | 1 - 0 | Southend Utd. |
| after extra time |
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| 2005/2006 | F.A. Cup | 2nd Round | Sat 03 Dec | Southend Utd. | 1 - 2 | Milton Keynes |
| League Cup | 1st Round | Mon 22 Aug | Southend Utd. | 0 - 3 | Southampton |
| (Associate Members) | Southern Section 1st Round | Tue 18 Oct | Rushden & D. | 1 - 0 | Southend Utd. |
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| 2004/2005 | F.A. Cup | 1st Round | Fri 12 Nov | Southend Utd. | 0 - 3 | Luton Town |
| League Cup | 1st Round | Tue 24 Aug | West Ham Utd. | 2 - 0 | Southend Utd. |
| (Associate Members) | Final | Sun 10 Apr | Wrexham | 2 - 0 | Southend Utd. |
| after extra time, 90 minutes 0-0, at the Millenium Stadium, Cardiff |
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| 2003/2004 | F.A. Cup | 3rd Round Replay | Wed 14 Jan | Scarborough | 1 - 0 | Southend Utd. |
| League Cup | 1st Round | Tue 12 Aug | Southend Utd. | 2 - 3 | Swindon Town |
| (Associate Members) | Final | Sun 21 Mar | Blackpool | 2 - 0 | Southend Utd. |
| at the Millennium Stadium, Cardiff |
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| 2002/2003 | F.A. Cup | 2nd Round Replay | Tue 17 Dec | Bournemouth | 3 - 2 | Southend Utd. |
| League Cup | 1st Round | Tue 10 Sep | Southend Utd. | 1 - 4 | Wimbledon |
| (Associate Members) | Southern Section 1st Round | Tue 22 Oct | Swindon Town | 6 - 1 | Southend Utd. |
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| 2001/2002 | F.A. Cup | 3rd Round | Tue 08 Jan | Southend Utd. | 1 - 3 | Tranmere Rvs. |
| League Cup | 1st Round | Wed 22 Aug | Birmingham C. | 3 - 0 | Southend Utd. |
| (Associate Members) | Southern Section 2nd Round | Tue 30 Oct | Southend Utd. | 0 - 2 | Bristol City |
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| 2000/2001 | F.A. Cup | 3rd Round | Sat 06 Jan | Southend Utd. | 0 - 1 | Kingstonian |
| League Cup | 1st Round | Tue 05 Sep | Birmingham C. | 0 - 0 | Southend Utd. |
| (Associate Members) | Southern Section Final | Tue 20 Mar | Brentford | 2 - 1 | Southend Utd. |
| Brentford won 4-2 on aggregate |
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| 1999/2000 | F.A. Cup | 1st Round | Sat 30 Oct | Torquay Utd. | 1 - 0 | Southend Utd. |
| League Cup | 1st Round | Tue 24 Aug | Oxford Utd. | 1 - 0 | Southend Utd. |
| Oxford United won 3-0 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 07 Dec | Southend Utd. | 0 - 1 | Cheltenham T. |
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| 1998/1999 | F.A. Cup | 1st Round | Sat 14 Nov | Southend Utd. | 0 - 1 | Doncaster Rvs. |
| League Cup | 2nd Round | Tue 22 Sep | Southend Utd. | 0 - 4 | Coventry City |
| Coventry City won 5-0 on aggregate |
| (Associate Members) | Southern Section 2nd Round | Tue 05 Jan | Exeter City | 3 - 1 | Southend Utd. |
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| 1997/1998 | F.A. Cup | 2nd Round | Sat 06 Dec | Fulham | 1 - 0 | Southend Utd. |
| League Cup | 2nd Round | Wed 01 Oct | Derby County | 5 - 0 | Southend Utd. |
| Derby County won 6-0 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 09 Dec | Southend Utd. | 0 - 1 | Wycombe Wdrs. |
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| 1996/1997 | F.A. Cup | 3rd Round | Wed 15 Jan | Leicester City | 2 - 0 | Southend Utd. |
| League Cup | 1st Round | Tue 03 Sep | Fulham | 1 - 2 | Southend Utd. |
| Fulham won 3-2 on aggregate |
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| 1995/1996 | F.A. Cup | 3rd Round | Sat 06 Jan | West Ham Utd. | 2 - 0 | Southend Utd. |
| League Cup | 2nd Round | Tue 03 Oct | Crystal Palace | 2 - 0 | Southend Utd. |
| Crystal Palace won 4-2 on aggregate |
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| 1994/1995 | F.A. Cup | 3rd Round | Sat 07 Jan | Southampton | 2 - 0 | Southend Utd. |
| League Cup | 1st Round | Tue 23 Aug | Watford | 1 - 0 | Southend Utd. |
| Watford won 1-0 on aggregate |
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| 1993/1994 | F.A. Cup | 3rd Round | Tue 18 Jan | Luton Town | 1 - 0 | Southend Utd. |
| League Cup | 1st Round | Tue 24 Aug | Barnet | 1 - 1 | Southend Utd. |
| Barnet won 3-1 on aggregate |
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| 1992/1993 | F.A. Cup | 5th Round | Sat 13 Feb | Sheff. Wed. | 2 - 0 | Southend Utd. |
| League Cup | 2nd Round | Wed 07 Oct | Derby County | 7 - 0 | Southend Utd. |
| Derby County won 7-1 on aggregate |
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| 1991/1992 | F.A. Cup | 3rd Round | Sat 04 Jan | Everton | 1 - 0 | Southend Utd. |
| League Cup | 1st Round | Wed 28 Aug | Southend Utd. | 1 - 1 | Watford |
| Watford won 3-1 on aggregate |
| (Full Members) | Southern Section 2nd Round | Tue 22 Oct | Crystal Palace | 4 - 2 | Southend Utd. |
| after extra time, 90 minutes 2-2 |
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| 1990/1991 | F.A. Cup | 1st Round | Sat 17 Nov | Leyton Orient | 3 - 2 | Southend Utd. |
| League Cup | 2nd Round | Tue 09 Oct | Southend Utd. | 1 - 2 | Crystal Palace |
| Crystal Palace won 10-1 on aggregate |
| (Associate Members) | Southern Section Semi-Final | Tue 05 Mar | Southend Utd. | 0 - 3 | Brentford |
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| 1989/1990 | F.A. Cup | 1st Round | Sat 18 Nov | Aylesbury U. | 1 - 0 | Southend Utd. |
| League Cup | 2nd Round | Wed 04 Oct | Southend Utd. | 3 - 2 | Tottenham H. |
| aggregate 3-3, Tottenham Hotspur won on away goals rule |
| (Associate Members) | Southern Section Quarter-Final | Tue 30 Jan | Walsall | 4 - 1 | Southend Utd. |
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| 1988/1989 | F.A. Cup | 1st Round | Sat 19 Nov | Bristol City | 3 - 1 | Southend Utd. |
| League Cup | 2nd Round | Tue 11 Oct | Southend Utd. | 1 - 2 | Derby County |
| Derby County won 3-1 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 17 Jan | Northampton | 2 - 1 | Southend Utd. |
| after extra time, 90 minutes 0-0 |
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| 1987/1988 | F.A. Cup | 1st Round Replay | Tue 17 Nov | Walsall | 2 - 1 | Southend Utd. |
| League Cup | 3rd Round | Tue 27 Oct | Ipswich Town | 1 - 0 | Southend Utd. |
| (Associate Members) | Southern Section 1st Round | Wed 20 Jan | Brighton & HA | 4 - 2 | Southend Utd. |
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| 1986/1987 | F.A. Cup | 2nd Round Replay | Wed 10 Dec | Northampton | 3 - 2 | Southend Utd. |
| League Cup | 2nd Round | Wed 08 Oct | Man. City | 2 - 1 | Southend Utd. |
| Manchester City won 2-1 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 27 Jan | Bristol City | 1 - 0 | Southend Utd. |
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| 1985/1986 | F.A. Cup | 1st Round | Sat 16 Nov | Southend Utd. | 0 - 1 | Newport Co. |
| League Cup | 1st Round | Tue 03 Sep | Gillingham | 2 - 0 | Southend Utd. |
| Gillingham won 3-1 on aggregate |
| (Associate Members) | Southern Section Preliminary Round Group Six | Thu 13 Mar | Southend Utd. | 1 - 3 | Northampton |
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| 1984/1985 | F.A. Cup | 1st Round Replay | Wed 21 Nov | Colchester U. | 3 - 2 | Southend Utd. |
| after extra time, 90 minutes ?-? |
| League Cup | 1st Round | Wed 05 Sep | Southend Utd. | 0 - 0 | Orient |
| Leyton Orient won 2-1 on aggregate |
| (Associate Members) | Southern Section 1st Round | Tue 26 Feb | Millwall | 3 - 1 | Southend Utd. |
| Millwall won 5-1 on aggregate |
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| 1983/1984 | F.A. Cup | 1st Round Replay | Tue 22 Nov | Plymouth Arg. | 2 - 0 | Southend Utd. |
| after extra time, 90 minutes 0-0 |
| League Cup | 1st Round | Tue 13 Sep | Wimbledon | 6 - 4 | Southend Utd. |
| Wimbledon won 6-5 on aggregate |
| (Associate Members) | Southern Section Quarter-Final | Tue 03 Apr | Southend Utd. | 1 - 2 | Bristol Rvs. |
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| 1982/1983 | F.A. Cup | 3rd Round 2nd Replay | Mon 24 Jan | Sheff. Wed. | 2 - 1 | Southend Utd. |
| League Cup | 1st Round | Tue 14 Sep | Fulham | 4 - 2 | Southend Utd. |
| Fulham won 4-3 on aggregate |
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| 1981/1982 | F.A. Cup | 1st Round | Sat 21 Nov | Hereford Utd. | 3 - 1 | Southend Utd. |
| League Cup | 1st Round | Wed 16 Sep | Portsmouth | 4 - 1 | Southend Utd. |
| Portsmouth won 4-1 on aggregate |
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| 1980/1981 | F.A. Cup | 1st Round | Sat 22 Nov | Southend Utd. | 0 - 1 | Hereford Utd. |
| League Cup | 1st Round | Wed 13 Aug | Oxford Utd. | 2 - 0 | Southend Utd. |
| Oxford United won 2-1 on aggregate |
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| 1979/1980 | F.A. Cup | 2nd Round Replay | Tue 18 Dec | Harlow Town | 1 - 0 | Southend Utd. |
| League Cup | 3rd Round 2nd Replay | Mon 08 Oct | West Ham Utd. | 5 - 1 | Southend Utd. |
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| 1978/1979 | F.A. Cup | 3rd Round Replay | Wed 17 Jan | Liverpool | 3 - 0 | Southend Utd. |
| League Cup | 1st Round | Tue 15 Aug | Wimbledon | 4 - 1 | Southend Utd. |
| Wimbledon won 4-2 on aggregate |
|
| 1977/1978 | F.A. Cup | 3rd Round | Sat 07 Jan | Derby County | 3 - 2 | Southend Utd. |
| League Cup | 1st Round | Tue 16 Aug | Northampton | 2 - 1 | Southend Utd. |
| Northampton Town won 5-3 on aggregate |
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| 1976/1977 | F.A. Cup | 3rd Round | Sat 08 Jan | Southend Utd. | 0 - 4 | Chester |
| League Cup | 1st Round | Tue 17 Aug | Brighton & HA | 2 - 1 | Southend Utd. |
| Brighton & Hove Albion won 3-2 on aggregate |
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| 1975/1976 | F.A. Cup | 5th Round | Sat 14 Feb | Derby County | 1 - 0 | Southend Utd. |
| League Cup | 1st Round | Wed 27 Aug | Peterborough | 3 - 0 | Southend Utd. |
| Peterborough United won 3-2 on aggregate |
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| 1974/1975 | F.A. Cup | 3rd Round Replay | Tue 07 Jan | Q.P.R. | 2 - 0 | Southend Utd. |
| League Cup | 2nd Round | Wed 11 Sep | Southend Utd. | 0 - 2 | Colchester U. |
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| 1973/1974 | F.A. Cup | 3rd Round | Sat 05 Jan | Peterborough | 3 - 1 | Southend Utd. |
| League Cup | 1st Round | Tue 28 Aug | Portsmouth | 2 - 1 | Southend Utd. |
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| 1972/1973 | F.A. Cup | 1st Round | Sat 18 Nov | Southend Utd. | 0 - 2 | Aldershot |
| League Cup | 2nd Round | Wed 06 Sep | Southend Utd. | 0 - 1 | Chelsea |
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| 1971/1972 | F.A. Cup | 2nd Round | Sat 11 Dec | Bournemouth | 2 - 0 | Southend Utd. |
| League Cup | 1st Round Replay | Mon 23 Aug | Southend Utd. | 1 - 2 | Aldershot |
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| 1970/1971 | F.A. Cup | 3rd Round | Mon 11 Jan | Southend Utd. | 0 - 3 | Carlisle Utd. |
| League Cup | 1st Round | Tue 18 Aug | Charlton Ath. | 3 - 0 | Southend Utd. |
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| 1969/1970 | F.A. Cup | 1st Round Replay | Wed 19 Nov | Gillingham | 2 - 0 | Southend Utd. |
| League Cup | 3rd Round | Wed 24 Sep | Bradford City | 2 - 1 | Southend Utd. |
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| 1968/1969 | F.A. Cup | 4th Round | Sat 25 Jan | Mansfield Town | 2 - 1 | Southend Utd. |
| League Cup | 2nd Round | Wed 04 Sep | Wolves | 1 - 0 | Southend Utd. |
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| 1967/1968 | F.A. Cup | 1st Round | Wed 13 Dec | Brighton & HA | 1 - 0 | Southend Utd. |
| League Cup | 2nd Round | Wed 13 Sep | Southend Utd. | 1 - 2 | Darlington |
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| 1966/1967 | F.A. Cup | 1st Round | Sat 26 Nov | Watford | 1 - 0 | Southend Utd. |
| League Cup | 1st Round Replay | Wed 31 Aug | Gillingham | 2 - 0 | Southend Utd. |
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| 1965/1966 | F.A. Cup | 3rd Round | Sat 22 Jan | Rotherham U. | 3 - 2 | Southend Utd. |
| League Cup | 2nd Round | Wed 22 Sep | Reading | 5 - 1 | Southend Utd. |
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| 1964/1965 | F.A. Cup | 1st Round | Sat 14 Nov | Luton Town | 1 - 0 | Southend Utd. |
| League Cup | 3rd Round | Wed 14 Oct | Stoke City | 3 - 1 | Southend Utd. |
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| 1963/1964 | F.A. Cup | 1st Round | Sat 16 Nov | Yeovil Town | 1 - 0 | Southend Utd. |
| League Cup | 3rd Round | Wed 16 Oct | Swindon Town | 3 - 0 | Southend Utd. |
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| 1962/1963 | F.A. Cup | 2nd Round | Sat 24 Nov | Southend Utd. | 0 - 2 | Watford |
| League Cup | 2nd Round | Wed 26 Sep | Southend Utd. | 2 - 3 | Notts. County |
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| 1961/1962 | F.A. Cup | 1st Round | Sat 04 Nov | Southend Utd. | 0 - 2 | Watford |
| League Cup | 1st Round | Wed 13 Sep | Southend Utd. | 0 - 1 | Stoke City |
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| 1960/1961 | F.A. Cup | 2nd Round | Sat 26 Nov | Gillingham | 3 - 2 | Southend Utd. |
| League Cup | 2nd Round | Tue 25 Oct | Rochdale | 5 - 2 | Southend Utd. |
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| 1959/1960 | F.A. Cup | 2nd Round | Sat 05 Dec | Southampton | 3 - 0 | Southend Utd. |
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| 1958/1959 | F.A. Cup | 1st Round Replay | Thu 20 Nov | Yeovil Town | 1 - 0 | Southend Utd. |
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| 1957/1958 | F.A. Cup | 3rd Round Replay | Wed 08 Jan | Southend Utd. | 2 - 3 | Liverpool |
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| 1956/1957 | F.A. Cup | 4th Round | Sat 26 Jan | Southend Utd. | 1 - 6 | Birmingham C. |
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| 1955/1956 | F.A. Cup | 4th Round | Sat 28 Jan | Southend Utd. | 0 - 1 | Man. City |
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| 1954/1955 | F.A. Cup | 3rd Round | Sat 08 Jan | Everton | 3 - 1 | Southend Utd. |
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| 1953/1954 | F.A. Cup | 2nd Round | Sat 12 Dec | Southend Utd. | 1 - 2 | Chesterfield |
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| 1952/1953 | F.A. Cup | 1st Round | Sat 22 Nov | Bath City | 3 - 1 | Southend Utd. |
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| 1951/1952 | F.A. Cup | 5th Round | Sat 23 Feb | Southend Utd. | 1 - 2 | Sheff. Utd. |
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| 1950/1951 | F.A. Cup | 1st Round | Wed 29 Nov | Southend Utd. | 0 - 3 | Swindon Town |
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| 1949/1950 | F.A. Cup | 3rd Round | Sat 07 Jan | Blackpool | 4 - 0 | Southend Utd. |
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| 1948/1949 | F.A. Cup | 1st Round | Sat 04 Dec | Southend Utd. | 1 - 2 | Swansea Town |
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| 1947/1948 | F.A. Cup | 1st Round | Sat 29 Nov | Newport Co. | 3 - 2 | Southend Utd. |
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| 1946/1947 | F.A. Cup | 3rd Round | Sat 11 Jan | Everton | 4 - 2 | Southend Utd. |
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| 1945/1946 | F.A. Cup | 1st Round | Sat 24 Nov | Southend Utd. | 0 - 3 | Watford |
| Watford won 4-1 on aggregate |
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| 1938/1939 | F.A. Cup | 4th Round | Sat 21 Jan | Blackburn R. | 4 - 2 | Southend Utd. |
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| 1937/1938 | F.A. Cup | 3rd Round Replay | Wed 12 Jan | Barnsley | 2 - 1 | Southend Utd. |
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| 1936/1937 | F.A. Cup | 2nd Round Replay | Wed 16 Dec | York City | 2 - 1 | Southend Utd. |
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| 1935/1936 | F.A. Cup | 3rd Round Replay | Wed 15 Jan | Southend Utd. | 1 - 2 | Tottenham H. |
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| 1934/1935 | F.A. Cup | 3rd Round | Sat 12 Jan | Southend Utd. | 0 - 4 | Sheff. Utd. |
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| 1933/1934 | F.A. Cup | 3rd Round | Sat 13 Jan | Tranmere Rvs. | 3 - 0 | Southend Utd. |
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| 1932/1933 | F.A. Cup | 4th Round | Sat 28 Jan | Southend Utd. | 2 - 3 | Derby County |
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| 1931/1932 | F.A. Cup | 2nd Round | Sat 12 Dec | Northampton | 3 - 0 | Southend Utd. |
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| 1930/1931 | F.A. Cup | 1st Round | Sat 29 Nov | Southend Utd. | 0 - 1 | Torquay Utd. |
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| 1929/1930 | F.A. Cup | 2nd Round | Sat 14 Dec | Southend Utd. | 1 - 4 | York City |
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| 1928/1929 | F.A. Cup | 1st Round | Sat 24 Nov | Luton Town | 5 - 1 | Southend Utd. |
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| 1927/1928 | F.A. Cup | 2nd Round | Sat 10 Dec | Gillingham | 2 - 0 | Southend Utd. |
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| 1926/1927 | F.A. Cup | 2nd Round | Sat 11 Dec | Reading | 3 - 2 | Southend Utd. |
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| 1925/1926 | F.A. Cup | 5th Round | Sat 20 Feb | Southend Utd. | 0 - 1 | Nottm. Forest |
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| 1921/1922 | F.A. Cup | 2nd Round | Sat 28 Jan | Southend Utd. | 0 - 1 | Swansea Town |
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| 1920/1921 | F.A. Cup | 3rd Round | Sat 19 Feb | Southend Utd. | 1 - 4 | Tottenham H. |
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| 1919/1920 | F.A. Cup | 1st Round | Sat 10 Jan | Sheff. Utd. | 3 - 0 | Southend Utd. |
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| 1914/1915 | F.A. Cup | 2nd Round | Sat 30 Jan | Burnley | 6 - 0 | Southend Utd. |
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| 1913/1914 | F.A. Cup | 1st Round | Sat 10 Jan | Birmingham | 2 - 1 | Southend Utd. |
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| 1912/1913 | F.A. Cup | 1st Round | Sat 11 Jan | Chelsea | 5 - 2 | Southend Utd. |
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| 1910/1911 | F.A. Cup | 1st Round | Sat 14 Jan | Blackburn R. | 5 - 1 | |
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