Chetwynde was founded as ''Our Lady's Chetwynde School'' in 1938 by Sister Aquinas and her nuns as a girls' school. In 1976, the school became mixed and independent from the church, though it retained its Catholic faith and ethos. Under Margaret Stones, the school's first headteacher, Chetwynde achieved high levels of
sporting and academic success. The next headteacher was Isobel Nixon; during her time as headmistress the school dropped the "Our Lady's" prefix from its title and the school's record of high academic and extra-curricular achievement was maintained. New laboratories were built with the help of the John Fisher Foundation and many other modernisations took place. It was initially a junior school for children up to age 11. In 1984, the age range was extended to 16. By then the school had outgrown its premises on Abbey Road and moved to its current site. The
Sixth Form was opened in 1989. The first male headteacher, Russell Collier, was appointed in 2010. From 2014 to 2019, the headteacher of Chetwynde School was Ms Sian Jeffreys, and as of September 2019 onwards, the current headteacher is Mr Stephen Jefferson. On 25 May 2012, it was announced that the school would remain open in September after an eleventh hour purchase from a currently unnamed purchaser. The school remained under the leadership of the headmaster Russell Collier with a new board of governors, the majority from the Chetwynde Support Group (CSG). The school began to offer new bursary programs to make it more accessible to the local community and to increase enrollment. ==Free school application==