| Season |
Competition |
Round Reached |
Date |
Home |
Score |
Away |
| 2012/2013 | F.A. Cup | 3rd Round Replay | Tue 15 Jan | Brentford | 2 - 1 | Southend Utd. |
| League Cup | 1st Round | Tue 14 Aug | Peterborough | 4 - 0 | Southend Utd. |
| (Associate Members) | Southern Final | Wed 20 Feb | Southend Utd. | 2 - 2 | Leyton Orient |
| Southend United won 3-2 on aggregate |
| 2011/2012 | F.A. Cup | 2nd Round Replay | Tue 13 Dec | Oldham Ath. | 1 - 0 | Southend Utd. |
| League Cup | 1st Round | Tue 09 Aug | Southend Utd. | 1 - 1 | Leyton Orient |
| after extra time, 90 minutes 1-1, Leyton Orient won 4-3 on penalties |
| (Associate Members) | Southern Semi-Final | Tue 06 Dec | Southend Utd. | 1 - 2 | Swindon Town |
| 2010/2011 | F.A. Cup | 1st Round Replay | Tue 16 Nov | Southend Utd. | 2 - 2 | Macclesfield |
| after extra time, 90 minutes 1-1, Macclesfield Town won 5-3 on penalties |
| League Cup | 2nd Round | Tue 24 Aug | Wolves | 2 - 1 | Southend Utd. |
| after extra time, 90 minutes 1-1 |
| (Associate Members) | Southern Quarter-Final | Tue 09 Nov | Southend Utd. | 0 - 1 | Charlton Ath. |
| 2009/2010 | F.A. Cup | 1st Round | Sat 07 Nov | Gillingham | 3 - 0 | Southend Utd. |
| League Cup | 2nd Round | Tue 25 Aug | Hull City | 3 - 1 | Southend Utd. |
| (Associate Members) | Southern 2nd Round | Tue 06 Oct | Milton Keynes | 2 - 0 | Southend Utd. |
| 2008/2009 | F.A. Cup | 3rd Round Replay | Wed 14 Jan | Southend Utd. | 1 - 4 | Chelsea |
| League Cup | 1st Round | Tue 12 Aug | Southend Utd. | 0 - 1 | Cheltenham T. |
| after extra time |
| (Associate Members) | Southern 1st Round | Tue 02 Sep | Southend Utd. | 2 - 4 | Leyton Orient |
| 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 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 |
| 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 |
| 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 1st Round | Tue 18 Oct | Rushden & D. | 1 - 0 | Southend Utd. |
| 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 |
| 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 |
| 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 1st Round | Tue 22 Oct | Swindon Town | 6 - 1 | Southend Utd. |
| 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 2nd Round | Tue 30 Oct | Southend Utd. | 0 - 2 | Bristol City |
| 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 Final | Tue 20 Mar | Brentford | 2 - 1 | Southend Utd. |
| Brentford won 4-2 on aggregate |
| 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 1st Round | Tue 07 Dec | Southend Utd. | 0 - 1 | Cheltenham T. |
| 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 2nd Round | Tue 05 Jan | Exeter City | 3 - 1 | Southend Utd. |
| 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 1st Round | Tue 09 Dec | Southend Utd. | 0 - 1 | Wycombe Wdrs. |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 Semi-Final | Tue 05 Mar | Southend Utd. | 0 - 3 | Brentford |
| 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 Quarter-Final | Tue 30 Jan | Walsall | 4 - 1 | Southend Utd. |
| 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 1st Round | Tue 17 Jan | Northampton | 2 - 1 | Southend Utd. |
| after extra time, 90 minutes 0-0 |
| 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 1st Round | Wed 20 Jan | Brighton & HA | 4 - 2 | Southend Utd. |
| 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 1st Round | Tue 27 Jan | Bristol City | 1 - 0 | Southend Utd. |
