| Season | Winners | Season | Winners | Season | Winners |
| 1902-03 | Southend | 1949-50 | Ilford | 1986-87 | Wanstead & Woodford |
| 1903-04 | East London | 1950-51 | Ilford | 1987-88 | Ilford |
| 1904-05 | Ilford | 1951-52 | Ilford | 1988-89 | Ilford |
| 1905-06 | Southend | 1952-53 | Southend | 1989-90 | Ilford |
| 1906-07 | Southend | 1953-54 | Ilford | 1990-91 | Powdermill |
| 1907-08 | Leyton | 1954-55 | Ilford | 1991-92 | Ilford |
| 1908-09 | Leyton | 1955-56 | Ilford | 1992-93 | Writtle |
| 1909-10 | Leyton | 1956-57 | Southend | 1993-94 | Powdermill |
| 1910-11 | Leyton | 1957-58 | Ilford | 1994-95 | Ilford |
| 1911-12 | Leyton | 1958-59 | Southend | 1995-96 | Eastbrook |
| 1912-13 | Leyton | 1959-60 | Southend | 1996-97 | Southend |
| 1913-14 | East Ham and Ilford | 1960-61 | Ilford | 1997-98 | Writtle |
| 1914-15 | Leyton | 1961-62 | Southend | 1998-99 | Ilford |
| 1919-20 | Leyton | 1962-63 | Ilford | 1999-2000 | Writtle |
| 1920-21 | Ilford | 1963-64 | Old Parkonians | 2000-01 | Writtle |
| 1921-22 | Southend | 1964-65 | Walthamstow, Chingford & Leyton | 2001-02 | Powdermill |
| 1922-23 | Southend | 1965-66 | Ilford | 2002-03 | Writtle |
| 1923-24 | Leyton | 1966-67 | Ilford | 2003-04 | Writtle |
| 1924-25 | Leyton | 1967-68 | Waltham Forest | 2004-05 | Wanstead & Woodford |
| 1925-26 | Southend | 1968-69 | Romford | 2005-06 | Writtle |
| 1926-27 | Southend | 1969-70 | Ilford | 2006-07 | Writtle |
| 1927-28 | Ilford | 1970-71 | Waltham Forest | 2007-08 | Writtle |
| 1928-29 | Leyton | 1971-72 | East Ham | 2008-09 | Writtle |
| 1929-30 | Ilford | 1972-73 | East Ham | 2009-10 | Writtle |
| 1930-31 | Chelmsford | 1973-74 | Old Parkonians | 2010-11 | Writtle |
| 1931-32 | Chelmsford | 1974-75 | Wanstead & Woodford | 2011-12 | Writtle |
| 1932-33 | Leyton | 1975-76 | Ilford | 2012-13 | Writtle |
| 1933-34 | Ilford | 1976-77 | Wanstead & Woodford | 2013-14 | Writtle |
| 1934-35 | Southend | 1977-78 | Upminster | 2014-15 | Wanstead & Woodford |
| 1935-36 | Leyton | 1978-79 | Upminster | 2015-16 | Writtle |
| 1936-37 | Ilford | 1979-80 | Upminster | 2016-17 | Writtle |
| 1937-38 | Leyton | 1980-81 | Writtle | 2017-18 | Writtle |
| 1938-39 | Leyton and Southend | 1981-82 | Wanstead & Woodford | 2018-19 | Wanstead & Woodford |
| 1945-46 | Upminster | 1982-83 | Wanstead & Woodford | 2019-20 | Barking |
| 1946-47 | Southend | 1983-84 | Wanstead & Woodford | 2020-21 | No competition |
| 1947-48 | Southend | 1984-85 | Ilford | 2021-22 | |
| 1948-49 | Southend | 1985-86 | Upminster | ||
Records:
| Most wins: | Most consecutive wins – 9 | Longest Hegemony |
| Ilford 27 | Writtle, 2005-06 – 2013-14 | For 17 seasons: (i) 1946/47 – 1962/63, the Championship was won by only Ilford or Southend. Ilford (9), Southend (8). (ii) 2002-03 – 2018-19, the Championship was won by only Writtle or Wanstead & Woodford. Writtle (14), Wanstead & Woodford (3). |
| Writtle 19 | ||
| Southend 18, Leyton 16 | ||
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