[1] The school was established in 1646 at the height of the English Civil War, when a wealthy London merchant, Richard Aldworth of Stanlake Park, left the Corporation of Reading the sum of £4,000, the proceeds of which were to be devoted to "the education and upbringing of twenty poor male children, being the children of honest, religious poor men in the town of Reading."

Aldworth, who had been a governor of Christ's Hospital in London, modelled the new foundation on his former school, the boys being required to wear the Bluecoat attire of gown, yellow stockings, and buckled shoes.

Despite many difficulties at the outset, the School flourished and even received generous subventions from local benefactors such as William Malthus and John West.

Malthus also left a certain sum for an annual sermon to be preached to the boys, a tradition still maintained in Reading at the end of each summer term.

The existing Holme Park mansion is situated within a few hundred yards of Rich's own manor house, an old residence which in turn had been built near an ancient ruined palace that had belonged to the Bishops of Salisbury long before the Norman Conquest in 1066.

Described by the Headmaster, Bernard Inge, as "an act of faith", and following a local fundraising appeal sponsored by the Bishop of Reading, the Mayor, and Corporation, the Trustees acquired the Holme Park estate.

Further classrooms including modern facilities for technology and computing were added in the 1980s in response to rising educational expectations and growing pupil numbers.

The newly completed 'James McArthur Sixth Form Center' (named after a previous headmaster) was opened in the autumn of 2010 by Old Blue and MP for Reading West Alok Sharma.

On Remembrance Day 2014, 100 years after the outbreak of the First World War, a 13-year-old pupil, Harry Hayes, who is a member of the School's Combined Cadet Force (CCF), planted the last poppy of the Blood Swept Lands and Seas of Red, a 2014 work of installation art placed in the moat of the Tower of London, England on 11 November 2014, specifically commemorating the centenary of the outbreak of World War I (28 July 1914).

[4] Fiona Carrier, a former private piano teacher, pleaded guilty at Oxford Magistrates Court to indecent Assault at her own house in the 1990s.