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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 complete collection of bound books, gathering Old Oakhamian Magazines copies, from 1899 to 2002. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

A prospectus promoting studying at Oakham School in 1956. Contents: Introduction; School Terms & holidays; Timetable; Chapel services; Curriculum; Reports; Boarding Houses; Diet; Health; Absence & Leaves; Games; C.C.F.; Scouts and Cubs; Clothes; Entry; Fees; Pocket Money; Notice of Leaving; Scholarships; Leaving Scholarships; Expenses; Appointments with Headmaster; Day Boys; Old Oakhamian Club. Six double-pages A to F.

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).

Extract from a 1940 prospectus, published in the Old Oakhamian Magazine. Content: Size; Staff; Fees; Curriculum; Timetable; Diet & Tuck boxes; Games; Activities outside the classroom; Day Boys. Three pages A to C.

A sermon preached on Sunday 15 December 1957 in Oakham School Chapel by the Headmaster, G. Talbot Griffith. Five pages A to E.

A calendar of events in the Spring term 1958. Three double-pages A to C.

A calendar of events in the Winter term 1937.

A note from Headmaster G. Talbot Griffiths to Geoffrey Liebert regarding the awarding of Sport Colours in December 1950.

This sub-series focusses on the every day running of School House. The bulk of the sub-series is punishment books and record books from the 1950s and 1960s.