FA Cup 2020/21, First Round Proper |
 | 07.11.2020 |  | Boreham Wood | – | Southend United | | 3:3 aet
(1:0, 2:2),
pen. 4:3 * |
| Borehamwood |
FA Cup 2018/19, First Round Proper |
| 10.11.2018 | | Southend United | – | Crawley Town | | 1:1 (1:0) |
| Southend-on-Sea |
FA Cup 2012/13, Third Round Proper |
| 05.01.2013 | | Southend United | – | Brentford | | 2:2 (1:2) |
| Southend-on-Sea |
FA Cup 2012/13, Second Round Proper |
| 11.12.2012 | | Southend United | – | Bury | | 1:1 aet
(0:0, 1:1),
pen. 3:2 * |
| Southend-on-Sea |
FA Cup 2012/13, Second Round Proper |
| 01.12.2012 | | Bury | – | Southend United | | 1:1 (1:1) |
| Bury |
FA Cup 2011/12, Second Round Proper |
| 03.12.2011 | | Southend United | – | Oldham Athletic | | 1:1 (0:1) |
| Southend-on-Sea |
FA Cup 2011/12, First Round Proper |
| 12.11.2011 | | Preston North End | – | Southend United | | 0:0 |
| Preston |
FA Cup 2010/11, First Round Proper |
| 16.11.2010 | | Southend United | – | Macclesfield Town | | 2:2 aet
(0:0, 1:1),
pen. 3:5 * |
| Southend-on-Sea |
FA Cup 2010/11, First Round Proper |
| 06.11.2010 | | Macclesfield Town | – | Southend United | | 2:2 (1:1) |
| Macclesfield |
FA Cup 2008/09, Third Round Proper |
| 03.01.2009 | | Chelsea | – | Southend United | | 1:1 (1:0) |
| London |
FA Cup 2008/09, First Round Proper |
| 08.11.2008 | | AFC Telford United | – | Southend United | | 2:2 (0:1) |
| Telford |
FA Cup 2007/08, Second Round Proper |
| 01.12.2007 | | Oxford United | – | Southend United | | 0:0 |
| Oxford |
FA Cup 2006/07, Third Round Proper |
| 06.01.2007 | | Southend United | – | Barnsley | | 1:1 (0:0) |
| Southend-on-Sea |
FA Cup 2003/04, Third Round Proper |
| 03.01.2004 | | Southend United | – | Scarborough | | 1:1 (1:0) |
| Southend-on-Sea |
FA Cup 2003/04, First Round Proper |
| 09.11.2003 | | Southend United | – | Canvey Island | | 1:1 (1:1) |
| Southend-on-Sea |
FA Cup 2002/03, Second Round Proper |
| 07.12.2002 | | Southend United | – | AFC Bournemouth | | 1:1 (0:1) |
| Southend-on-Sea |
FA Cup 2002/03, First Round Proper |
| 16.11.2002 | | Southend United | – | Hartlepool United | | 1:1 (1:1) |
| Southend-on-Sea |
FA Cup 2001/02, Second Round Proper |
| 08.12.2001 | | Chesterfield | – | Southend United | | 1:1 (0:0) |
| Chesterfield |
FA Cup 2000/01, First Round Proper |
| 17.11.2000 | | Torquay United | – | Southend United | | 1:1 (1:1) |
| Torquay |
FA Cup 1987/88, First Round Proper |
| 14.11.1987 | | Southend United | – | Walsall | | 0:0 |
| Southend-on-Sea |
FA Cup 1986/87, Second Round Proper |
| 05.12.1986 | | Southend United | – | Northampton Town | | 4:4 (1:1) |
| Southend-on-Sea |
FA Cup 1984/85, First Round Proper |
| 17.11.1984 | | Southend United | – | Colchester United | | 2:2 |
| |
FA Cup 1983/84, First Round Proper |
| 19.11.1983 | | Southend United | – | Plymouth Argyle | | 0:0 |
| |
FA Cup 1982/83, Third Round Proper |
| 11.01.1983 | | Sheffield Wednesday | – | Southend United | | 2:2 aet * |
| |
FA Cup 1982/83, Third Round Proper |
| 08.01.1983 | | Southend United | – | Sheffield Wednesday | | 0:0 |
| |
FA Cup 1979/80, Second Round Proper |
| 15.12.1979 | | Southend United | – | Harlow Town | | 1:1 |
| |
FA Cup 1978/79, Third Round Proper |
| 10.01.1979 | | Southend United | – | Liverpool | | 0:0 |
| |
FA Cup 1978/79, Second Round Proper |
| 16.12.1978 | | Watford | – | Southend United | | 1:1 |
| |
FA Cup 1977/78, Second Round Proper |
| 17.12.1977 | | AP Leamington | – | Southend United | | 0:0 |
| |
FA Cup 1976/77, First Round Proper |
| 20.11.1976 | | Exeter City | – | Southend United | | 1:1 |
| Exeter |
FA Cup 1974/75, Third Round Proper |
| 04.01.1975 | | Southend United | – | Queens Park Rangers | | 2:2 |
| |
FA Cup 1969/70, First Round Proper |
| 15.11.1969 | | Southend United | – | Gillingham | | 0:0 |
| |
FA Cup 1958/59, First Round Proper |
| 15.11.1958 | | Southend United | – | Yeovil Town | | 0:0 |
| |
FA Cup 1957/58, Third Round Proper |
| 04.01.1958 | | Liverpool | – | Southend United | | 1:1 |
| |
FA Cup 1957/58, Second Round Proper |
| 07.12.1957 | | Torquay United | – | Southend United | | 1:1 |
| |
FA Cup 1949/50, Second Round Proper |
| 10.12.1949 |  | Wrexham | – | Southend United | | 2:2 |
| |
FA Cup 1945/46, First Round Proper |
| 17.11.1945 | | Watford | – | Southend United | | 1:1 |
| |
FA Cup 1938/39, Third Round Proper |
| 11.01.1939 | | Chesterfield | – | Southend United | | 1:1 |
| |
FA Cup 1937/38, Third Round Proper |
| 08.01.1938 | | Southend United | – | Barnsley | | 2:2 |
| |
FA Cup 1936/37, Second Round Proper |
| 12.12.1936 | | Southend United | – | York City | | 3:3 |
| |
FA Cup 1936/37, First Round Proper |
| 28.11.1936 | | Crystal Palace | – | Southend United | | 1:1 |
| |
FA Cup 1935/36, Third Round Proper |
| 11.01.1936 | | Tottenham Hotspur | – | Southend United | | 4:4 |
| |
FA Cup 1932/33, Third Round Proper |
| 14.01.1933 | | Watford | – | Southend United | | 1:1 |
| |
FA Cup 1932/33, First Round Proper |
| 26.11.1932 | | Southend United | – | Exeter City | | 1:1 |
| |
FA Cup 1914/15, First Round Proper |
| 16.01.1915 | | Bristol Rovers | – | Southend United | | 0:0 |
| |
FA Cup 1909/10, Second Round Proper |
| 05.02.1910 | | Southend United | – | Queens Park Rangers | | 0:0 |
| |
FA Cup 1909/10, First Round Proper |
| 15.01.1910 | | Gainsborough Trinity | – | Southend United | | 1:1 |
| |
