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A photograph of a boys' Cricket 1st XI. Date '1887' is written (modern addition) but does not coincide with names of the pupils on the photograph and their leaving year. Date is now thought to be in 1882 or 1883, according to cricket records, even if some names do not match. Some names written on the item are not on the register and have been amended below in 'Access Points'.

A collection of photographs and art work relating to the whole School Campus, in particular aerial photographs from 1937 of the School and the town, and a file of individual photographs of buildings around the campus. The oldest items in this sub-series date back to the 19th century.

This file focusses on photographs on the School Campus throughout the years. Some photographs are of the whole campus, in particular aerial photographs taken by Aerofilms Ltd, and some are collection of individual buildings, taken by Companies or individuals.

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

This sub-series contains books used by pupils during services in chapel or books published by staff or Old Oakhamians and given to the school. A large part of this sub-series contains hymns books compiled by Rev T.C.H. Clare ('29).

Newspaper cuttings printed on one page reporting on the 1979 rugby visit from Japan School to Oakham School.

Three photographs of Old School, All Saints Church and School House in their original frame. The photographs were taken by John Burton & Sons, Photographers and Artists, Leicester, in activity from 1863 to 1911.

A sepia toned, oval framed photos of School House. The photograph was taken by John Burton & Sons, and the date is estimated between 1863 and 1911.

A prospectus promoting studying at Oakham School in 1937. 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; O.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. Nine double-pages A to I. Enclosed are a form of application for admission (J) and a clothes list for the Junior House (K).