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| 1927-28 Clesco |
| 1928-29 W. Ham Ment. |
| 1929-30 Clesco |
| 1930-31 Upminster Wand |
| 1931-32 Clesco |
| 1932-33 Roneo |
| 1933-34 Clesco |
| 1934-35 Roneo |
| 1935-36 Clesco |
| 1936-37 Ford Sports |
| 1937-38 S. Essex W'works |
| 1938-39 S. Essex W'works |
| 1939-45 In Abeyance |
| 1945-46 Upminster |
| 1946-47 Rainham Town |
| 1947-48 Orsett Old Boys |
| 1948-49 Hornchurch Athletic |
| 1949-50 Hornchurch Athletic |
| 1950-51 * |
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| 1972-73 Five Star Alexander |
| 1973-74 Rise Sports |
| 1974-75 Brittons |
| 1975-76 Herongate 'A' |
| 1976-77 Bishops Park Rangers |
| 1977-78 British Legion Sports |
| 1978-79 Riverside 74 |
| 1979-80 Brentwood 'A' |
| 1980-81 Tilbury Scruttons |
| 1981-82 Triangle |
| 1982-83 Fiesta |
| 1983-84 Fiesta |
| 1984-85 Rainham Athletic |
| 1985-86 Blue Royals |
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| 1947-48 Stifford Athletic |
| 1948-49 Dagenham Dock |
| 1949-50 Harold Wood |
| 1950-51 * |
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| 1986-87 H & S Wanders |
| 1987-88 Brentwood Manor |
| 1988-89 Ardleigh Green |
| 1989-90 Harold Park |
| 1990-91 Duckwood |
| 1991-92 Manford Way |
| 1992-93 Spartan Athletic |
| 1993-94 Granby |
| 1994-95 Balgores |
| 1995-96 Lawson |
| 1996-97 Technique |
| 1997-98 Brabazon Sports |
| 1998-99 Canning Town |
| 1999-00 Canning Town |
| 2000-01 Alex |
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