The school was founded during the reign of Henry VII and was established as a 'common school' by the Corporation of the Borough of Bridgnorth.
Following an Act of Parliament that dissolved chantry chapels, an endowment of £8 a year was set aside from the revenues of the Chantry of St Leonard’s for a schoolmaster to run a grammar school there.
The first named Schoolmaster was Reuben Steenton.
A barn that had been used as the chapel of St John the Baptist, first housed the school. This was replaced by a building in St Leonard's Close known as the 'Old Grammar School'.
Sir John Hayward, an MP for the town, bequeathed £100 to the school in his will. Previously, his father, Sir Rowland Hayward, a successful Bridgnorth merchant who went on to become Lord Mayor of London twice, endowed the school with an annual payment of £20.
Sir William Whitmore of Apley Park leased a new building in St Leonard’s Close to the town. This included three individual dwellings, with the scholars housed in one, the schoolmaster in another and the incumbent of St Leonard’s in the third.
Edward Careswell of Bobbington left money in his will to enable scholars from six Shropshire schools, one of which was the Bridgnorth Grammar School, to have a subsidised university education at Christ Church College Oxford.
There were just ten boys at the school when Dr Thomas Rowley became Headmaster. Having studied at Christ Church, Oxford, the school's reputation increased and pupil numbers rose to about 150.
A.J. Balfour’s Education Act created Education Authorities and Shropshire County Council began to exercise its duty as an Education Authority.
The school passed into the control of Shropshire County Council – it was the County Council’s first secondary school.
The new grammar school building at Northgate opened with three members of staff and 93 boys.
The Girls’ High School moved, along with the boys’ school, into the new premises but boys and girls were kept separate.
During the First World War, 39 ‘old boys’ including three masters, lost their lives in active service and, in commemoration, a War Memorial Board containing the names of the fallen was unveiled in the school.
The financial climate of the times helped to force the decision to fully amalgamate the two schools.
The school was reorganised and became a mixed school.
The school played a big part locally in the war effort, its buildings and playing fields being used by the Air Training Corps, the Women’s Junior Air Corps, the Scouts, the Boys’ and Girls’ Clubs, the Fire Brigade, the Homeguard and the RAF.
The school expanded and a building programme began, including a new dining hall and kitchen and a domestic science room.
New chemistry and biology laboratories were built.
The school was granted voluntary controlled status by the Ministry of Education.
The school's name was changed from Bridgnorth Grammar School to Bridgnorth Endowed School, when it began the transition from grammar to comprehensive.
New science block opened.
The Sports and Leisure Centre was opened by Princess Anne.
A team of students swam the English Channel in a record time of 13 hours 34 minutes. They were the first Salopians to do this since Captain Webb who was also the first person ever to swim the Channel.
With over 1000 pupils and 63 teachers, the building programme continued and the school flourished.
The school was named as being among the top ten comprehensives in Britain for the quality of its A Level results.
The library was moved to the heart of the building and a new administration block was built. More computer rooms were added and the provision for Sixth Form was improved.
Building projects continued, including another large technology suite and expansion of the library.
The school was awarded specialist status as a Technology College.
A clock was erected on the outside of the main building to mark the school's 500th anniversary.
Bridgnorth Endowed School converted to become an academy school on 1st March 2013.