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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.

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).

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).

This series focusses on documents relating to Brian Welford' career at Oakham School as Master-in-charge of Rugby in the 1970s and 1980s. Also contains documents relating to the history of rugby and Old Oakhamians, kept by Mr Welford in his personal files.

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 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.