[2][3] The site was purchased in 1660 by a grocer, Henry Box, who decided to endow a school in his hometown after becoming a successful businessman in London.

[6] In the 17th and 18th century, Witney Grammar School grounded the sons of merchants, manufacturers and minor gentry in classical curriculum, including Latin, Greek and Hebrew in preparation for entry to university.

The staff included two resident assistant masters, a visiting drill master, and a resident female music teacher; subjects offered included English, French, Latin, arithmetic, natural science, drawing, singing, and bookkeeping.

These subjects were intended to attract more children of professional tradesmen and farmers, therefore increasing the number of pupils at the school.

[5] The Henry Box School plays an annual football game against the Abingdon and Witney College in memory of former student Kevin Mott.

[24] 27% of A level grades awarded were A*/A,[25] and 14.4% of sixth form pupils achieved AAB or above including 2 facilitating subjects, below the national average of 17%.

[26] Subjects offered include: Art and Design, Biology, Business Studies, Chemistry, Childcare, Drama, Economics, English Language, English Literature, Food Technology, French, Geography, German, Graphics, History, ICT, Mathematics, Music, Physics, Psychology, Religious Studies, Resistant Materials, Sociology, Systems and Control and Textiles.

In addition to this, several students currently represent Great Britain and England in sports ranging from golf to equestrian to baseball.

Students take part in the Kids' Lit Quiz[32] annually and the school also hosts author visits such as Chris Bradford and Andy Briggs.

[35] The school's new music block, including a recording studio and sound-proof practice and teaching rooms, was opened on 26 November 2010 by David Cameron, Prime Minister.

To celebrate the opening of the music block, students recorded a cover of Take That's Greatest Day which was then uploaded onto YouTube.

The Henry Box School has a large and successful sixth form, from which the majority of students go on to higher education including the most competitive universities such as Oxford and Cambridge.

Admission to the sixth form is conditional on gaining an average of 42 GCSE points overall, including a C grade in English Language and B in the subjects to be studied at A Level.