1895 1896 Club formed with HQ at the Victory Inn, and a pitch on the South side of the Green.
1901 1902 Affiliated to ECFA and played first competitive game in Essex Junior Cup, losing 3 0 to Parkeston Athletic.
1903 1904 Joined Colchester & District League, Division 2.
1905 1906 Switched to Clacton & District League.
1906 1907 Played in both leagues.
1907 1908 Withdrew from Colchester League, but when Clacton League was too late in affiliating Bentley were forced to play friendlies, and lost several of their best players. Continued to play friendlies and cup games until 1 st World War.
1912 1913 Moved HQ across the road to the Plough Inn, where the dressing room was in the old stable.
1919 1920 Joined the Tendring Hundred League. Started a Reserve side, which later played in the Tendring Hundred League and then the Brightlingsea and District League.
1924 1925 1 st Team won the Tendring Hundred League.
1925 1926 Joined the Border League, Division 2, Section B, and have enjoyed unbroken membership of the League ever since.
1928 1929 Won Division 2.
1930 1931 Runners-up in Division 2.
1931 1932 Won Division 2.
1935 1936 Runners-up in Division 2. Reserves joined Border League, Division 3 until 2 nd World Ward.
1936 1937 1 st Team won Division 2.
1946 1947 Reserves joined Tendring Hundred League.
1947 1948 1 st Team won Division 1. Runners-up in Division 1 KO up.
1948 1949 Runners-up Division 1 KO Cup.
1949 1950 Reserved joined Colchester & East Essex League.
1950 1951 1 st Team were runners-up in Division 1.
Sept 1951 The club played its first game on the current prepared pitch near the Mill House.
1952 1953 Runners-up in Division 1.
1953 1954 Reserves rejoined the Tendring Hundred League until its demise.
1957 1958 1 st team won Division 1 KO Cup on an 11 3 aggregate again Hedingham United.
1959 1960 Opened new dressing rooms, built on the site of an old war-time Nissen hut. These were much nearer the pitch than the Plough, where both teams had to change in the same room, round a full-size billiard table.
1967 1968 Reserves joined Colchester & East Essex League until 1975 1976 when they joined the Border League.
1977 1978 1 st Team were runners-up in Division 1, but their facilities were not good enough for promotion.
1980 1981 Runners-up in Division 1 again, and this time promoted.
1983 1984 Relegated after spending their only three seasons ever in the Premier Division.
1984 1985 Relegated from Division 1, after finishing bottom.
1987 1988 Reserves failed in bid for re-election after coming bottom of Division 3, four times in a row, and have played in the Colchester League since then.
1989 1990 Third place good enough for 1 st Team to be promoted to Division 1.
1991 1992 Relegated to Division 2, where they still play.
1994 - 1995 Runners-up in the Tommy Thompson Cup
Area Finalists in the Essex Junior Cup finished 3rd and promoted to the Border Premier League.
2006 - 2007 A Team Formed.
2007 - 2008 A Team Runners up in Lexden Cup.
2009 - 2010 Runners-up in Harwich Charity Cup.
2009 - 2010 Clubhouse and changing rooms refurbished.
2011 - 2012 Reserve Cup Runners up and Tommy Thompson Cup Runners Up
2014- 2015 First Team - Withdrawn from Premier division / Veterans Team - Formed & League runners up
2015 -2016 Veterans Team - League runners up and Winners of fair play award.
2016 -2017 First Team - Division Two Border League Winners / Reserve team - Reformed. Boxted Six a Side Winners.
2017 - 2018 First team - Border League Divison One Winners./ Veterans Runners Up North Essex Cup.
Some of Great Bentleys Leading Lights over the Years
P Z Clark, founder member of the Club, who had spells as Captain, Secretary and Chairman, before becoming a referee.
Joe Syrett, larger than life Secretary, whose enthusiasm helped to rejuvenate the Clubs ailing fortunes prior to World War 1.
George A Cowell, a Club Member since 1900, Mr Cowell went on to hold the key positions of the Secretary and then Treasurer, right up to his death in 1947.
George Seaman, long-serving player from 1919 1920, captained the side to success in the Tendring Hundred League and the Border League. George held office as Secretary, then after the 2 nd World Ward, Vice-Chairman and Treasurer, until 1957.
David Plummer, began as a player in 1932 and elected as Vice-Chairman in 1948, Chairman in 1951, and Secretary in 1959, until he stood down in 1967.
Pat Hynes, Secretary from 1946 to 1959, Pat was a key figure in Bentleys move to a new pitch, and later, new dressing rooms.
Richard Morton, in more recent times, was Chairman for over twenty years, taking on the position when the club was going through turbulent times, and helping to steer them into much calmer waters.