| 07 Dec 1929 | Southend United | Home | League | 1-1 | Edmonds | 7,622 |
| 12 Apr 1930 | Southend United | Away | League | 1-4 | Edmonds | 6,282 |
| 06 Dec 1930 | Southend United | Wembley Stadium | League | 3-1 | Fowler (2), Tricker | 1,916 |
| 11 Apr 1931 | Southend United | Away | League | 0-2 | | 5,791 |
| 03 Oct 1931 | Southend United | Home | League | 2-4 | Jack, Fowler | 17,072 |
| 13 Feb 1932 | Southend United | Away | League | 3-1 | Best, Tricker, Fletcher | 4,714 |
| 19 Nov 1932 | Southend United | Away | League | 3-3 | Dimmock, Best, G Phillips | 4,901 |
| 01 Apr 1933 | Southend United | Home | League | 0-0 | | 4,677 |
| 09 Sep 1933 | Southend United | Away | League | 1-2 | Morris | 8,927 |
| 20 Jan 1934 | Southend United | Home | League | 5-2 | Halliday (3), Rigby (2) | 8,091 |
| 22 Dec 1934 | Southend United | Away | League | 2-0 | Taylor, Mayson | 5,586 |
| 04 May 1935 | Southend United | Home | League | 3-0 | Crawford (2), Foster | 6,560 |
| 28 Sep 1935 | Southend United | Away | League | 1-2 | Fogg | 10,148 |
| 01 Feb 1936 | Southend United | Home | League | 3-0 | Crawford (3) | 9,496 |
| 17 Apr 1937 | Southend United | Away | League | 0-0 | | 5,166 |
| 29 Apr 1937 | Southend United | Home | League | 3-0 | Rossiter (2), Fletcher | 2,541 |
| 15 Sep 1937 | Southend United | Away | League | 2-1 | Crawford (2) | 5,587 |
| 07 May 1938 | Southend United | Home | League | 1-1 | H Smith | 5,560 |
| 22 Oct 1938 | Southend United | Home | League | 5-0 | Williams (3), Dodds, H Smith | 9,744 |
| 25 Feb 1939 | Southend United | Away | League | 0-1 | | 4,497 |
| 04 Sep 1946 | Southend United | Home | League | 1-1 | Baynham | 6,799 |
| 19 Sep 1946 | Southend United | Away | League | 0-0 | | 7,610 |
| 13 Sep 1947 | Southend United | Away | League | 1-2 | Hunt | 10,019 |
| 31 Jan 1948 | Southend United | Home | League | 2-0 | Neary, Pullen | 13,306 |
| 04 Sep 1948 | Southend United | Away | League | 2-2 | Neary, Dryden | 13,245 |
| 15 Jan 1949 | Southend United | Home | League | 2-0 | Naylor, McGeachy | 9,377 |
| 06 Sep 1949 | Southend United | Away | League | 0-2 | | 12,119 |
| 26 Nov 1949 | Southend United | Home | FAC r1 | 0-2 | | 17,932 |
| 06 May 1950 | Southend United | Home | League | 2-2 | McEwan, Pullan | 13,197 |
| 02 Sep 1950 | Southend United | Away | League | 1-0 | Pattison | 14,698 |
| 30 Dec 1950 | Southend United | Home | League | 1-1 | McGeachy | 7,793 |
| 29 Sep 1951 | Southend United | Away | League | 0-1 | | 11,700 |
| 09 Feb 1952 | Southend United | Home | League | 1-4 | Harris | 16,900 |
| 06 Sep 1952 | Southend United | Away | League | 0-1 | | 14,200 |
| 17 Jan 1953 | Southend United | Home | League | 3-0 | Pacey, Poulton (pen), Brown | 13,054 |
| 03 Oct 1953 | Southend United | Home | League | 1-1 | Pacey | 16,986 |
| 24 Feb 1954 | Southend United | Away | League | 1-2 | Facey | 4,500 |
| 27 Nov 1954 | Southend United | Home | League | 5-1 | Facey (pen), Rees (2), Morgan, Blizzard | 16,061 |
| 16 Apr 1955 | Southend United | Away | League | 2-1 | Rees, Fisher | 8,000 |
| 03 Sep 1955 | Southend United | Away | League | 0-0 | | 21,000 |
| 31 Dec 1955 | Southend United | Home | League | 3-0 | Heckman (2), Burgess | 19,690 |
| 15 Aug 1981 | Southend United | Home | AMC | 2-0 | Jennings, Chiedozie | 1,806 |
| 16 Aug 1982 | Southend United | Away | AMC | 1-1 | P Taylor | 2,069 |
| 29 Oct 1982 | Southend United | Away | League | 1-1 | Cunningham | 5,139 |
| 13 Mar 1983 | Southend United | Home | League | 1-1 | Houchen | 3,073 |
| 21 Oct 1983 | Southend United | Away | League | 0-3 | | 4,116 |
| 26 Feb 1984 | Southend United | Home | League | 1-0 | Brooks | 3,001 |
| 28 Aug 1984 | Southend United | Home | LC r1-1 | 2-1 | Cunningham, Sussex | 2,685 |
| 05 Sep 1984 | Southend United | Away | LC r1-2 | 0-0 | | 2,340 |
| 23 Aug 1985 | Southend United | Away | League | 1-5 | Jones | 3,643 |
| 21 Dec 1985 | Southend United | Home | League | 3-0 | Brooks (pen), Juryeff, Shinners | 3,545 |
| 04 Oct 1986 | Southend United | Home | League | 1-0 | Cornwell | 3,634 |
| 27 Mar 1987 | Southend United | Away | League | 1-2 | Cunningham | 4,160 |
| 17 Nov 1990 | Southend United | Home | FAC r1 | 3-2 | Castle (2), Nugent | 6,095 |
| 09 Apr 1991 | Southend United | Home | League | 0-1 | | 6,297 |
| 07 May 1991 | Southend United | Away | League | 1-1 | Day | 8,759 |
| 17 Oct 1998 | Southend United | Away | League | 2-2 | Lockwood, Inglethorpe | 6,700 |
| 03 Apr 1999 | Southend United | Home | League | 0-3 | | 6,537 |
| 30 Aug 1999 | Southend United | Away | League | 1-1 | Walschaerts | 5,991 |
| 05 Feb 2000 | Southend United | Home | League | 2-1 | Watts, Brkovic | 5,972 |
| 26 Dec 2000 | Southend United | Away | League | 1-0 | Griffiths | 9,595 |
| 20 Jan 2001 | Southend United | Home | League | 0-2 | | 6,859 |
| 01 Sep 2001 | Southend United | Away | League | 2-1 | Smith, Constantine | 5,853 |
| 12 Mar 2002 | Southend United | Home | League | 2-1 | Christie, Nugent | 4,840 |
| 29 Oct 2002 | Southend United | Home | League | 2-1 | Iriekpen, Whelan (og) | 5,343 |
| 22 Mar 2003 | Southend United | Away | League | 0-1 | | 4,148 |
| 18 Oct 2003 | Southend United | Away | League | 2-1 | Alexander, McSweeney (og) | 6,077 |
| 21 Feb 2004 | Southend United | Home | League | 2-1 | Broughton (og), Bramble (og) | 6,119 |
| 07 Dec 2004 | Southend United | Home | League | 2-2 | Lockwood (pen), Scott | 3,852 |
| 15 Apr 2005 | Southend United | Away | League | 1-0 | Mackie | 9,189 |
| 11 Aug 2007 | Southend United | Away | League | 2-1 | Thornton, Boyd | 9,828 |
| 02 Feb 2008 | Southend United | Home | League | 2-2 | Boyd (pen), Ibehre | 6,886 |
| 02 Sep 2008 | Southend United | Away | JPT s.r1 | 4-2 | Jarvis, Chambers, Melligan, Boyd (pen) | 3,499 |
| 26 Sep 2008 | Southend United | Away | League | 0-3 | | 9,261 |
| 20 Jan 2009 | Southend United | Home | League | 1-1 | Boyd | 3,835 |
| 04 Sep 2009 | Southend United | Away | League | 0-3 | | 8,836 |
| 28 Dec 2009 | Southend United | Home | League | 1-2 | Chambers | 5,680 |
| 09 Aug 2011 | Southend United | Away | LC r1 | 1-1* | Richardson | 4,847 |
| 05 Feb 2013 | Southend United | Home | JPT s.fn1 | 0-1 | | 5,359 |
| 20 Feb 2013 | Southend United | Away | JPT s.fn2 | 2-2 | Batt, Mooney | 9,421 |
| 04 Oct 2016 | Southend United | Away | CT Group | 0-1 | | 2,383 |
| 03 Sep 2019 | Southend United | Home | FLT Group | 2-0 | Happe, Gorman | 1,562 |
| 29 Dec 2020 | Southend United | Home | League | 2-0 | McAnuff, Wilkinson | – |
| 24 Apr 2021 | Southend United | Away | League | 1-2 | Dennis | – |
| * Leyton Orient won 4-3 on Penalties |