[2] "… the like sume of twenty pounds yearly out of the said lands at Wavendon I give unto my wellbeloved friend Mr. William Tothill Esquire and Mr William Pennyman Esquire to erect a free gramar schoole in Amersam in the County of Bucks to be established by Deede of Feofment or otherwise as their wisdome can devise The towne and pish allotinge the Churche house for the schoole house or my successor a tenemt in the occupation of Enoch Wyar now or of late for the dwellinge house of the schoole maister whome I will to be chosen by my exequitrix my successor and Mr. Tothill afterwards by my successor and sixe of the eldest Feoffees and cheefest This I leave as a testimony of my loce to them and theire children.

Each year the boys at Challoner's celebrate Founder's Day where they attend St Mary's Church in Old Amersham where Robert Chaloner was rector.

By 1937, Challoner's was incorporated into the state system of education and by the early 1950s, the school had about 350 boys and girls on roll.

[citation needed] The continued expansion of the grammar school to its present size of over 1,350 students saw major building projects in the 1950s, 1980s, and 1990s, followed by the construction of a large astroturf pitch and improvements to the sports fields.

In 2005, the school celebrated the 100th anniversary of the move to the current site on Chesham Road, also building the Centenary Sports Pitch.

[5] Since the school founded its robotics team in 2015,[citation needed] Challoner's has competed in national and international competitions.

[6] In 2018, a team entered into PiWars, a competition involving Raspberry Pi computers hosted at the University of Cambridge.

[8] In March 2018 the society competed at SPIMUN (St Petersburg International Model United Nations) where five students won awards.