Page in course of construction.
We have constructed this table from the engravings on the Division II trophy (subject to proofreading), with the 25 seasons from 1995-96 to 2019-20 inclusive also being documented in David Millward’s Essex League records.
There is a division of styles for the engravings, with 1931-32 to 1986-87 giving just the name of the winning Club, but from 1987-88 onwards, team numbers are included; we have followed the trophy engraving.
There were two periods where there was no competition: i) WW II 1937-38 to 1944-45; ii) 2020-21 covid pandemic.
| Season | Winners | Season | Winners | Season | Winners |
|---|---|---|---|---|---|
| 1931-23 | Hornchurch | 1969-70 | East Ham | 1999-00 | Brentwood II |
| 1932-33 | Brentwood | 1970-71 | Ilford | 2000-01 | Grays I |
| 1933-34 | Romford | 1971-72 | Old Parkonians | 2001-02 | Maldon |
| 1934-35 | Upminster | 1972-73 | Old Parkonians | 2002-03 | Barking II |
| 1935-36 | Chelmsford | 1973-74 | Old Parkonians | 2003-04 | Upminster II |
| 1936-37 | Chelmsford | 1974-75 | Ilford | 2004-05 | Wanstead II |
| 1945-46 | Upminster | 1975-76 | Ilford | 2005-06 | Barking II |
| 1946-47 | Ilford | 1976-77 | Wanstead | 2006-07 | Bishop’s Stortford |
| 1947-48 | Leyton | 1977-78 | Upminster | 2007-08 | Basildon |
| 1948-49 | Upminster | 1978-79 | Harlow | 2008-09 | Wanstead II |
| 1949-50 | Old Parkonians | 1979-80 | Harlow | 2009-10 | Basildon |
| 1950-51 | East Ham | 1980-81 | Harlow | 2010-11 | Southend I |
| 1951-52 | Ilford | 1981-82 | Wanstead | 2011-12 | Ilford I |
| 1952-23 | Ford Sports & Southend | 1982-83 | Wanstead | 2012-13 | Southend I |
| 1953-54 | East Ham | 1983-84 | Ilford | 2013-14 | Upminster I |
| 1954-55 | Southend | 1984-85 | Wanstead | 2014-15 | Upminster II |
| 1955-56 | Southend | 1985-86 | Grays | 2015-16 | Wanstead II |
| 1956-57 | Romford | 1986-87 | Rayleigh | 2016-17 | Southend I |
| 1957-58 | Southend | 1987-88 | Ilford II | 2017-18 | Wanstead II |
| 1958-59 | Southend | 1988-89 | Barking II | 2018-19 | Brentwood |
| 1595-60 | Southend | 1989-90 | Grays I | 2019-20 | Southend I |
| 1960-61 | Southend | 1990-91 | Basildon | 2021-22 | Wanstead II |
| 1961-62 | West Ham | 1991-92 | East Ham I | 2022-23 | Ilford I |
| 1962-63 | Old Parkonians | 1992-93 | Eastbrook I | 2023-24 | Witham |
| 1963-64 | West Ham | 1993-94 | Bumbles Green | 2024-25 | Wanstead II |
| 1964-65 | Newham & East London | 1994-95 | Edmonton | ||
| 1965-66 | Ilford | 1995-96 | Grays I | ||
| 1966-67 | Southend | 1996-97 | Newham | ||
| 1967-68 | Southend | 1997-98 | Billericay | ||
| 1968-69 | East Ham/Upminster | 1998-99 | Basildon |