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This series is related to the charity work at Oakham School, including the fund raising and other events organised at school by staff, pupils, houses and the Oakham School Charities Association (OSCA) in aid of various charities and the local community.

This file contains a collection of photographs of Rushebrookes' 2022 leaving Sixth form girls (2023 School Leavers), since their very first year in house in 2018. Items were displayed by Kim Robinson, Housemistress, at the drinks reception prior to the girls' Leavers Ball on 30 June 2023.

A photograph of Rushebrookes' third form boarders on a trip to Leicester Gravity in the Winter term 2018.

This file focusses on admission prospectuses published throughout G. Talbot Griffith's headmastership.

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).

A collection of reports and financial statements, and letters, related to the activities of Oakham School Enterprises Ltd (OSEL), spanning from 1978 to 1995.

This file focusses on the organisation of various Oakham Art Festivals in the early 1990s.

Correspondence and an invoice relating to the catering arrangement for a buffet supper at the Oakham Festival for Marron, Dodds & Waite.

This sub-file focusses on the registration of Oakham School Enterprises Ltd with the Companies Registration Office, and includes correspondence and legal documents.

This file focusses on various documents relating to Sports at Oakham School.