| Premier Division |
| Year | Winner | Runner-Up |
| 1953-1954 | Holbrook united | Harlow United (Res) |
| 1954-1955 | Key Glass | Holbrook United |
| 1955-1956 | Holbrook United | Springham Rovers |
| 1956-1957 | Springham Rovers | Nettleswell v Burnt Mill |
| 1957-1958 | Nettleswell v Burnt Mill | Holbrook United |
| 1958-1959 | Standard | Vandyke United |
| 1959-1960 | Standard | British Matthews (Res) |
| 1960-1961 | Mark Hall Y.C. | Bovinger |
| 1961-1962 | Standard | Dorstel Press |
| 1962-1963 | Competition | Cancelled |
| 1963-1964 | Dorstel Press | British Matthews |
| 1964-1965 | Dorstel Press | Cossar |
| 1965-1966 | Cossor Sports | Sawbridgeworth |
| 1966-1967 | Tye Green | Standard |
| 1967-1968 | Cossor Sports | Inter-Nettleswell |
| 1968-1969 | Cossor Sports | Standard |
| 1969-1970 | Mark Hall Y,C. | Standard |
| 1970-1971 | Mark Hall Y,C | Standard |
| 1971-1972 | French | Standard |
| 1972-1973 | Alemite | Solent |
| 1973-1974 | Solent | Alemite |
| 1974-1975 | Solent | Burnt Mill School |
| 1975-1976 | Marco Penn | Coopersale |
| 1976-1977 | Solent | Pitney Bowes |
| 1977-1978 | Solent | Pitney Bowes |
| 1978-1979 | Solent | Pitney Bowes |
| 1979-1980 | Marco Penn | Alemite |
| 1981-1981 | Pitney Bowes | Little Parndon |
| 1981-1982 | Pitney Bowes | Delta |
| 1982-1983 | The Herald | Pitney Bowes |
| 1983-1984 | Fire | U G Delta |
| 1984-1985 | United Glass | Alemite |
| 1985-1986 | Alemite | United Glass |
| 1986-1987 | Little Parndon | United Glass |
| 1987-1988 | Phoenix | Little Parndon |
| 1988-1989 | Phoenix | Little Parndon |
| 1989-1990 | Phoenix | B.P. |
| 1990-1991 | Little Parndon | Hare |
| 1991-1992 | Composite | Old Town Athletic |
| 1992-1993 | H E Inflite | Trakback Royals |
| 1993-1994 | H E Inflite | Trakback Royals |
| 1994-1995 | Northbrooks | Maddox Road Sport |
| 1995 | LEAGUE | DISBANDED |
| Division 1 |
| Year | Winner | Runner-Up |
| 1955-1956 | High Lavers Res | Thiorley |
| 1956-1957 | Sunvic | Harlow Metal |
| 1957-1958 | Arlington Sports | Greaves and Thomas |
| 1958-1959 | Thorley | Lindsey Street C.A |
| 1959-1960 | Harlow Metal | Plyglass United |
| 1960-1961 | C.W.S. | Harlow Y.M.C.A. |
| 1961-1962 | Kores | Alemite |
| 1962-1963 | Competition | Cancelled |
| 1963-1964 | Harlow College | Mark Hall Rovers |
| Division 2 |
| Year | Winner | Runner-Up |
| 1964-1965 | Inter-Nettleswell | Epping Y.C. |
| Division 1 |
| Year | Winner | Runner-Up |
| 1964-1965 | Sawbridgeworth | Central Avenue |
| 1965-1966 | Inter-Nettleswell | Little Parndon |
| 1966-1967 | Nettleswell Dynamos | Tye Green Res |
| 1967-1968 | Northbrooks | Bovinger |
| 1968-1969 | Mark Hall Y.C. | Epping United |
| 1969-1970 | Standard Res | Matching United |
| 1970-1971 | Johnson Mathey | Cossor Res |
| 1971-1972 | Greaves and Thomas | Pitney Bowes |
| Division 2 |
| Year | Winner | Runner-Up |
| 1972-1973 | Bovinger | Coopersale |
| Division 1 |
| Year | Winner | Runner-Up |
| 1973-1974 | Burnt Mill Social | Pitney Bowes |
| 1974-1975 | Gilbey | Delta |
| 1975-1976 | Schreiber | Pitney Bowes Res |
| 1976-1977 | B.P. | Shark |
| 1977-1978 | Little Parndon Res | Foresters |
| 1978-1979 | Delta | White Admniral |
| 1979-1980 | Little Parndon Res | J.B. Sports |
| 1980-1981 | Little Parndon Res | LCS Rangers |
| 1981-1982 | The Sun | Haunt Athletic |
| 1982-1983 | Fire | Foresters |
| 1983-1984 | United Glass | Data Logic |
| 1984-1985 | Katherines | Phoenix |
| 1985-1986 | Permanite | Brookside |
| 1986-1987 | Milwards | New Ducts |
| 1987--1989 | No Competititon | No Competition |
| 1989-1990 | Vintners | Commonside Saints |
| 1990-1991 | Old Town Athletic | Kingsmoor Athletic |
| 1991 | DIVISION WITHDRAWN | FROM |
| Division 2 |
| Year | Winner | Runner-Up |
| 1956-1957 | Mark Hall Y.C. | Plyvan United |
| 1957-1958 | Vandyke | J.B. Sports |
| 1958-1959 | Plyglass United | Alemite Athletic |
| 1959-1960 | C.W.S. | Northbrooks |
| 1960-1961 | Sports | Mark Hall Rovers |
| 1961-1962 | British Oxygen | Tye Green Res |
| 1962-1963 | Competition | Cancelled |
| 1963-1964 | Coopersale United | Northbrooks Res |
| 1965-1966 | Nettleswell Dynamo | Alemite Athletics |
| 1966-1967 | Standard Res | Mark Hall Rangers |
| 1967-1968 | Mark Hall Y.C. | French |
| 1968-1969 | Harlow College | Potters Baptist |
| 1969-1981 | No Competition | No Competitiion |
| 1981-1982 | Fire | Theydon Bois |
| 1982-1983 | United Glass | Burtn Mill Social |
| 1983-1984 | Garnon O.B, | Data Logic |
| 1984 | DIVISION WITHDRAWN | FROM |