Although "those Gentlemen that have formerly been at that school" were invited to attend the School Feasts held at The Clothmakers' Hall in Mincing Lane between 1682 and 1685 and that, through the efforts of William Quennell, O.B. and Second Master at the time, there was an Old Brentwoods Chapel Service, a football match against the School and a Dinner at The White Hart, Brentwood (now the Sugar Hut) in 1868, it was not until 1899 that the Society of Old Brentwoods was formed.


The then Headmaster, Edwin Bean, and his son, Charles, along with Quennell who, by then , having served as Headmaster, was the Chairman of the Governors, were the prime movers in establishing the Society. Life membership was offered at a cost of half a guinea, an annual or biennial Dinner was to be organised and an Old Boys' column would appear in the Brentwoodian to keep members informed of what was happening.


The Rev. Cannon Quennell was appointed the first President at a meeting held on 15th. September, 1899 and C. E. W. Bean was the first Honorary Secretary. The first rule of the Society established its object as being: "to afford opportunities to members of meeting at regular intervals to keep members in touch with one and other and with the School ... and to promote the interests of the School."


Robert T. D. Stoneham became Secretary in 1905 and his enthusiasm and hard work ensured the success of the fledgling Society. Under Stoneham, Society members made a significant contribution to the building of the new Main School building, a precedent to the Old Brentwoods' support for subsequent building appeals and, in particular, for the Old Brentwoods' Memorial Appeals resulting in the Memorial Hall after the 1st. World War and the Pavilion and Chapel Memorial after the 1939-45 conflict.


In 1904 cricket fixtures had been arranged and in 1905 the Old Brentwoods Cricket Club was formed under the Presidency of Charles Kortright, O. B., captain of Essex and reputedly the fastest bowler of his time. In 1906, Stoneham, in addition to being Society Secretary, was also the Secretary of Brentwood Rovers Football Club, which included many Old Brentwood players. His efforts saw the amalgamation with the Brentwood Alumni F. C. - a club consisting entirely of Old Brentwoods - to form a side to play in the Arthur Dunn Cup competition.


Both Cricket and Football Clubs went into decline in 1913 and the advent of the 1st. World War meant they ceased to exist. In 1920, however, the Football club was re-established, thanks to the efforts of Secretary, Harold Parrish, but the Cricket Club was restricted to an annual match against the School, together with "Home Week" - six one-day games preceding August Bank Holiday, with many non-local Old Brentwoods sleeping in School House dormitory, thanks to Headmaster, J. F. Hough. The problem facing the Cricket Club, and one that still applies today, was the number of Old Brentwoods who preferred to play for Brentwood C. C. and in 1929 it was decided to concentrate on an annual tour - to become the Bunglers' Tour in 1947.


The Old Brentwoods Athletic Club was formed in 1927, the Old Brentwoods Golfing Society in 1931 along with a Tennis Club which, in 1934, became the Old Brentwoods Lawn Tennis and Squash Rackets Club.


This growth in Old Brentwoods' sporting activities required a clubhouse and grounds and, thanks to Headmaster, James Fisher Hough, what was to become the Burland Road ground was purchased. While the O. B. Football Club played on their own ground for the first time in 1939, the ground was acquired by Brentwood Urban District Council during the War and not returned to the Old Brentwoods until 1952. A new clubhouse was opened in 1954 and, as the ground provided a cricket square as well as two football pitches, the Old Brentwoods C.C. was re-established, with their opening game against an Essex XI being played in 1955.


The Old Brentwoods Rugby Club was formed in 1967, playing away games on Sundays for the first three seasons but then moving to a full fixture list for two sides on Saturdays in 1970. With the Rugby Club playing on Jim McTurk's "cow-patch" and then moving, via Queen Elizabeth College, to the council pitch at Bishops Hall, the demand on the Society's facilities, combining with the likelihood of a re-development of Brentwood town centre, meant that it was decided to sell the Burland Road ground in 1975 and look for a new headquarters for the Old Brentwoods.


Sporting activities were moved to the Essex Water Company's ground in Kenilworth Avenue, Harold Park for two years while the Society sought a suitable ground for purchase. Following ministerial enquiry, permission was granted to build the Aswells Road ground at Bentley and the Clubhouse, including squash courts, with its 22 acre grounds providing for Football, Cricket and Rugby was opened in June 1978. Tennis courts were built in the early eighties as a result of the fund raising drive led by Peter Griffiths, President in 1982, and the Clubhouse has benefited from the generous legacy left by Joe Hodgson (Master: 1934-74; President:1979)


Over the last 20 years the sporting activities have continued and the wonderful facilities have been enjoyed by not just Old Brentwoods but also many other members of the vibrant local Brentwood community with playing and suppporting sport forming the basis for strong friendships. So in 2016 the Society of Old Brentwoods formed the Old Brentwoods Club to manage the clubhouse and grounds and to promote friendship and participation in sport amongst former pupils of Brentwood School, friends of Brentwood School and members of the local community.