FA Cup 2021/22, Fourth Qualifying Round |
 | 16.10.2021 |  | Southend United | – | Chertsey Town | | 4:1 (2:1) |
| Southend-on-Sea |
FA Cup 2018/19, First Round Proper |
| 20.11.2018 | | Crawley Town | – | Southend United | | 2:6 aet
(0:2, 2:2) * |
| Crawley |
FA Cup 2013/14, Third Round Proper |
| 04.01.2014 | | Southend United | – | Millwall | | 4:1 (2:0) |
| Southend-on-Sea |
FA Cup 2013/14, Second Round Proper |
| 07.12.2013 | | Chesterfield | – | Southend United | | 1:3 (1:2) |
| Chesterfield |
FA Cup 2013/14, First Round Proper |
| 09.11.2013 | | Morecambe | – | Southend United | | 0:3 (0:2) |
| Morecambe |
FA Cup 2012/13, First Round Proper |
| 03.11.2012 | | Southend United | – | Stockport County | | 3:0 (1:0) |
| Southend-on-Sea |
FA Cup 2011/12, First Round Proper |
| 22.11.2011 | | Southend United | – | Preston North End | | 1:0 (0:0) * |
| Southend-on-Sea |
FA Cup 2008/09, Second Round Proper |
| 29.11.2008 | | Southend United | – | Luton Town | | 3:1 (1:0) |
| Southend-on-Sea |
FA Cup 2008/09, First Round Proper |
| 18.11.2008 | | Southend United | – | AFC Telford United | | 2:0 (0:0) * |
| Southend-on-Sea |
FA Cup 2007/08, Third Round Proper |
| 05.01.2008 | | Southend United | – | Dagenham & Redbridge | | 5:2 (1:1) |
| Southend-on-Sea |
FA Cup 2007/08, Second Round Proper |
| 11.12.2007 | | Southend United | – | Oxford United | | 3:0 (2:0) * |
| Southend-on-Sea |
FA Cup 2007/08, First Round Proper |
| 10.11.2007 | | Southend United | – | Rochdale | | 2:1 (2:1) |
| Southend-on-Sea |
FA Cup 2006/07, Third Round Proper |
| 16.01.2007 | | Barnsley | – | Southend United | | 0:2 (0:1) * |
| Barnsley |
FA Cup 2005/06, First Round Proper |
| 05.11.2005 | | Barnet | – | Southend United | | 0:1 (0:1) |
| London |
FA Cup 2003/04, Second Round Proper |
| 06.12.2003 | | Southend United | – | Lincoln City | | 3:0 (1:0) |
| Southend-on-Sea |
FA Cup 2003/04, First Round Proper |
| 19.11.2003 | | Canvey Island | – | Southend United | | 2:3 (2:1) * |
| Canvey Island |
FA Cup 2002/03, First Round Proper |
| 26.11.2002 | | Hartlepool United | – | Southend United | | 1:2 (0:0) * |
| Hartlepool |
FA Cup 2001/02, Second Round Proper |
| 18.12.2001 | | Southend United | – | Chesterfield | | 2:0 (1:0) * |
| Southend-on-Sea |
FA Cup 2001/02, First Round Proper |
| 17.11.2001 | | Southend United | – | Luton Town | | 3:2 (1:1) |
| Southend-on-Sea |
FA Cup 2000/01, Second Round Proper |
| 10.12.2000 | | Canvey Island | – | Southend United | | 1:2 (0:1) |
| Canvey Island |
FA Cup 2000/01, First Round Proper |
| 28.11.2000 | | Southend United | – | Torquay United | | 2:1 aet
(0:0, 1:1) * |
| Southend-on-Sea |
FA Cup 1997/98, First Round Proper |
| 15.11.1997 | | Woking | – | Southend United | | 0:2 (0:0) |
| Woking |
FA Cup 1992/93, Fourth Round Proper |
| 23.01.1993 | | Huddersfield Town | – | Southend United | | 1:2 (1:1) |
| Huddersfield |
FA Cup 1992/93, Third Round Proper |
| 13.01.1993 | | Southend United | – | Millwall | | 1:0 (1:0) |
| Southend-on-Sea |
FA Cup 1986/87, First Round Proper |
| 15.11.1986 | | Southend United | – | Halesowen Town | | 4:1 (2:1) |
| Southend-on-Sea |
FA Cup 1982/83, Second Round Proper |
| 11.12.1982 | | Southend United | – | Yeovil Town | | 3:0 |
| |
FA Cup 1982/83, First Round Proper |
| 20.11.1982 | | Bournemouth | – | Southend United | | 0:2 |
| |
FA Cup 1979/80, First Round Proper |
| 24.11.1979 | | Wealdstone | – | Southend United | | 0:1 |
| |
FA Cup 1978/79, Second Round Proper |
| 18.12.1978 | | Southend United | – | Watford | | 1:0 * |
| |
FA Cup 1978/79, First Round Proper |
| 25.11.1978 | | Southend United | – | Peterborough United | | 3:2 |
| |
FA Cup 1977/78, Second Round Proper |
| 19.12.1977 | | Southend United | – | AP Leamington | | 4:0 * |
| |
FA Cup 1977/78, First Round Proper |
| 26.11.1977 | | Torquay United | – | Southend United | | 1:2 |
| |
FA Cup 1976/77, Second Round Proper |
| 11.12.1976 | | Southend United | – | Newport County |  | 3:0 |
| Southend-on-Sea |
FA Cup 1976/77, First Round Proper |
| 22.11.1976 | | Southend United | – | Exeter City | | 2:1 * |
| Southend-on-Sea |
FA Cup 1975/76, Fourth Round Proper |
| 24.01.1976 | | Southend United | – | Cardiff City | | 2:1 |
| |
FA Cup 1975/76, Third Round Proper |
| 03.01.1976 | | Southend United | – | Brighton & Hove Albion | | 2:1 |
| |
FA Cup 1975/76, Second Round Proper |
| 13.12.1975 | | Southend United | – | Dover | | 4:1 |
| |
FA Cup 1975/76, First Round Proper |
| 22.11.1975 | | Southend United | – | Swansea City | | 2:0 |
| |
FA Cup 1974/75, Second Round Proper |
| 14.12.1974 | | Ilford | – | Southend United | | 0:2 |
| |
FA Cup 1974/75, First Round Proper |
| 23.11.1974 | | AP Leamington | – | Southend United | | 1:2 |
| |
FA Cup 1973/74, Second Round Proper |
| 15.12.1973 | | Southend United | – | Reading | | 2:0 |
| |
FA Cup 1973/74, First Round Proper |
| 24.11.1973 | | Southend United | – | Boreham Wood | | 3:0 |
| |
FA Cup 1971/72, First Round Proper |
| 20.11.1971 | | Southend United | – | Aston Villa | | 1:0 |
| |
FA Cup 1970/71, Second Round Proper |
| 12.12.1970 | | Southend United | – | Dagenham | | 1:0 |
| |
FA Cup 1970/71, First Round Proper |
| 21.11.1970 | | Southend United | – | Weymouth | | 7:0 |
| |
FA Cup 1968/69, Third Round Proper |
| 04.01.1969 | | Swindon Town | – | Southend United | | 0:2 |
| |
FA Cup 1968/69, Second Round Proper |
| 07.12.1968 | | Southend United | – | Brentwood Town | | 10:1 |
| |
FA Cup 1968/69, First Round Proper |
| 16.11.1968 | | Southend United | – | King's Lynn | | 9:0 |
| |
FA Cup 1965/66, Second Round Proper |
| 04.12.1965 | | Southend United | – | Watford | | 2:1 |
| |
FA Cup 1965/66, First Round Proper |
| 13.11.1965 | | Southend United | – | Notts County | | 3:1 |
| |
FA Cup 1962/63, First Round Proper |
| 03.11.1962 | | Southend United | – | Brighton & Hove Albion | | 2:1 |
| |
FA Cup 1960/61, First Round Proper |
| 05.11.1960 | | Clacton Town | – | Southend United | | 1:3 |
| |
FA Cup 1959/60, First Round Proper |
| 14.11.1959 | | Southend United | – | Oswestry Town | | 6:0 |
| |
FA Cup 1957/58, Second Round Proper |
| 11.12.1957 | | Southend United | – | Torquay United | | 2:1 * |
| |
FA Cup 1957/58, First Round Proper |
| 16.11.1957 | | Trowbridge Town | – | Southend United | | 0:2 |
| |
FA Cup 1956/57, Third Round Proper |
| 05.01.1957 | | Southend United | – | Liverpool | | 2:1 |
| |
FA Cup 1956/57, Second Round Proper |
| 08.12.1956 | | Hereford United | – | Southend United | | 2:3 |
| |
FA Cup 1956/57, First Round Proper |
| 17.11.1956 | | Colchester United | – | Southend United | | 1:4 |
| |
FA Cup 1955/56, Third Round Proper |
| 07.01.1956 | | Lincoln City | – | Southend United | | 2:3 |
| |
FA Cup 1955/56, Second Round Proper |
| 10.12.1955 | | Weymouth | – | Southend United | | 0:1 |
| |
FA Cup 1955/56, First Round Proper |
| 19.11.1955 | | Southend United | – | Queens Park Rangers | | 2:0 |
| |
FA Cup 1954/55, Second Round Proper |
| 11.12.1954 | | Bradford Park Avenue | – | Southend United | | 2:3 |
| |
FA Cup 1954/55, First Round Proper |
| 20.11.1954 | | Bristol City | – | Southend United | | 1:2 |
| |
FA Cup 1953/54, First Round Proper |
| 21.11.1953 | | Finchley | – | Southend United | | 1:3 |
| |
FA Cup 1951/52, Fourth Round Proper |
| 02.02.1952 | | Southend United | – | Bristol Rovers | | 2:1 |
| |
FA Cup 1951/52, Third Round Proper |
| 12.01.1952 | | Southend United | – | Southampton | | 3:0 |
| |
FA Cup 1951/52, Second Round Proper |
| 15.12.1951 | | Southend United | – | Oldham Athletic | | 5:0 |
| |
FA Cup 1951/52, First Round Proper |
| 24.11.1951 | | Southend United | – | Bournemouth | | 6:1 |
| |
FA Cup 1949/50, Second Round Proper |
| 15.12.1949 | | Southend United | – | Wrexham | | 2:0 * |
| |
FA Cup 1949/50, First Round Proper |
| 26.11.1949 | | Leyton Orient | – | Southend United | | 0:2 |
| |
FA Cup 1946/47, Second Round Proper |
| 14.12.1946 | | Barnet | – | Southend United | | 2:9 |
| |
FA Cup 1946/47, First Round Proper |
| 30.11.1946 | | Brush Sports | – | Southend United | | 1:6 |
| |
FA Cup 1938/39, Third Round Proper |
| 16.01.1939 | | Southend United | – | Chesterfield | | 4:3 * |
| |
FA Cup 1938/39, Second Round Proper |
| 10.12.1938 | | Port Vale | – | Southend United | | 0:1 |
| |
FA Cup 1938/39, First Round Proper |
| 26.11.1938 | | Southend United | – | Corinthians | | 3:0 |
| |
FA Cup 1937/38, Second Round Proper |
| 11.12.1937 | | Walthamstow Avenue | – | Southend United | | 0:1 |
| |
FA Cup 1937/38, First Round Proper |
| 27.11.1937 | | Corinthians | – | Southend United | | 0:2 |
| |
FA Cup 1936/37, First Round Proper |
| 02.12.1936 | | Southend United | – | Crystal Palace | | 2:0 * |
| |
FA Cup 1935/36, Second Round Proper |
| 14.12.1935 | | Southend United | – | Burton Town | | 5:0 |
| |
FA Cup 1935/36, First Round Proper |
| 30.11.1935 | | Newport County | – | Southend United | | 0:1 |
| |
FA Cup 1934/35, Second Round Proper |
| 08.12.1934 | | Wimbledon | – | Southend United | | 1:5 |
| |
FA Cup 1934/35, First Round Proper |
| 24.11.1934 | | Southend United | – | Golders Green | | 10:1 |
| |
FA Cup 1933/34, Second Round Proper |
| 09.12.1933 | | Southend United | – | Chester | | 2:1 |
| |
FA Cup 1933/34, First Round Proper |
| 25.11.1933 | | London Paper Mills | – | Southend United | | 0:1 |
| |
FA Cup 1932/33, Third Round Proper |
| 18.01.1933 | | Southend United | – | Watford | | 2:0 * |
| |
FA Cup 1932/33, Second Round Proper |
| 10.12.1932 | | Southend United | – | Scarborough | | 4:1 |
| |
FA Cup 1932/33, First Round Proper |
| 30.11.1932 | | Exeter City | – | Southend United | | 0:1 * |
| |
FA Cup 1931/32, First Round Proper |
| 28.11.1931 | | Torquay United | – | Southend United | | 1:3 |
| |
FA Cup 1929/30, First Round Proper |
| 30.11.1929 | | Southend United | – | Brentford | | 1:0 |
| |
FA Cup 1927/28, First Round Proper |
| 26.11.1927 | | Southend United | – | Wellington Town | | 1:0 |
| |
FA Cup 1926/27, First Round Proper |
| 27.11.1926 | | Dulwich Hamlet | – | Southend United | | 1:4 |
| |
FA Cup 1925/26, Fourth Round Proper |
| 30.01.1926 | | Southend United | – | Derby County | | 4:1 |
| |
FA Cup 1925/26, Third Round Proper |
| 09.01.1926 | | Southend United | – | Southport | | 5:2 |
| |
FA Cup 1925/26, Second Round Proper |
| 12.12.1925 | | Southend United | – | Gillingham | | 1:0 |
| |
FA Cup 1925/26, First Round Proper |
| 28.11.1925 | | Southend United | – | Dulwich Hamlet | | 5:1 |
| |
FA Cup 1921/22, First Round Proper |
| 07.01.1922 | | Worksop Town | – | Southend United | | 1:2 |
| |
FA Cup 1920/21, Second Round Proper |
| 29.01.1921 | | Southend United | – | Blackpool | | 1:0 |
| |
FA Cup 1920/21, First Round Proper |
| 08.01.1921 | | Southend United | – | Eccles United | | 5:1 |
| |
FA Cup 1914/15, First Round Proper |
| 23.01.1915 | | Southend United | – | Bristol Rovers | | 3:0 * |
| |
FA Cup 1909/10, First Round Proper |
| 19.01.1910 | | Southend United | – | Gainsborough Trinity | | 1:0 * |
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