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A prospectus promoting studying at Oakham School in 1902. Contents: Trustees & Staff; Subjects; Upper School & Lower School; Examinations; Boarding Houses; Library, Games & Extras; Terms; Holidays; Infectious Disease; Scholarships, Exhibitions & Prizes. Three double-pages A to C.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

A letter from the Headmaster Tony Little to Parents regarding the guidelines on parties during the term for day pupils and boarders.

A prospectus (A) promoting studying at Oakham School in 1935. Contents: Trustees; Staff; Admission; Work; Fees; Optional Payments; Absence & Remission of Fees; Health; Entrance Scholarships; Other Scholarships & Exhibitions; Buildings; Boarding Houses; Holidays & Hours; Games & Hobbies; School Societies; Expenses; Clothes List. Enclosed are corrections to prospectus (B), and a form of application for admission (C).

A prospectus promoting studying at Oakham School in 1943. Contents: Trustees & Staff; Foundation & History; The School today; Situation & Surroundings; Premises & Equipment; School Terms, Holidays, Timetable; Chapel Services, Religious Instruction; Curriculum; Libraries; Reports; Boarding Houses; School House, Wharflands, The Junior House; Clothes; Diet & Tuck Boxes; Health; Absence & Leave; Games; Physical Education; J.T.C.; Scouts; Activities outside the classroom; Entry, Fees, Remission of Fees for absence; Optional Payments, Extras; Pocket Money; Scholarships; Leaving Scholarships; Notice of leaving; Expenses; Appointments with the Headmaster; Day Boys; Publications; Old Oakhamian Club. Six double-pages A to F. Enclosed is a list of Trustees and Staff (G).

The Oakhamian Magazine and Old Oakhamian Magazine, recording the Summer term 2013. Contents: Features; Academic; Trips and Tours; Performing Arts; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; The Old Oakhamian Magazine; Foundation.

A photograph of Mary Hoyle and her husband at the official opening of Stevens house, standing in front of the commemorative plaque on 18 October 1989.

A photograph of pupils eating in the School House dining room in the 1960s. The photograph was taken by Photo-Reportage Ltd and the print number is stamped at the back: 157562. A number is written in the bottom right corner: 62.

A photograph of a boy on a bunk bed in a dorm, probably in Chapmans house in the 1950s/1960s. This photograph was taken by Photo-Reportage Ltd and the print number is stamped at the back: 147823. The number B23 is written on the front, in the bottom right corner.

Printed Powerpoint slides from a presentation on the centenary of Chapmans. Includes information on the school's founding, images of various school buildings from different times, campus maps and pupils; a history of Junior House/Chapmans House; and a list of Housemasters. Thirty-four pages A to AG.