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A photograph of the Boarding boys in Peterborough House in the academic year 2010-2011 under the Housemaster Steve Foster. Names of the pupils and staff are written below.

This series focuses on the Junior House/Chapmans pupils and staff since its opening in 1910. It first comprised the Junior Department with facilities for boys boarders and classrooms. The house was renamed Chapmans in September 1960, after Frank Emerson Chapman, first Housemaster of the Junior House; it became a Senior House. Most of the series is made of photographs, house photographs as well as more informal photographs.

Order of service for the Jerwoods Carol service in the School Chapel on 7 December 2007.

This sub-file contains various photographs of Val Harvey, Master of Jerwoods.

A programme of the Ancaster Performing Arts Soiree in aid of Cancer Research on 22 May 2006, with a list of the performers and musical numbers.

This sub-series focuses on the day-to-day running of Ancaster house and mostly contains house diaries. Items give information regarding the house, achievements of the girls and house events.

A certificate from the Diana Princess of Wales Memorial Award for Young People in recognition of students who have made a real difference to tackling bullying in their school communities awarded to Jerwoods Film Activity in the academic year 2005-2006.

A newspaper cutting from the Rutland Times of an article on Jim O'Kane, retiring after 33 years at Oakham School, and a photograph of the Lower School prizes winners at Speech Day.

A programme for Jerwoods New Year Concert on 13 January 2006 in the School Chapel, including a list of the musical numbers and a list of the performers and various bands.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.