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A School list of staff and pupils for the Spring term 1887. Contents: Staff; Upper Vi to Form I; Special prizes and Distinctions since last term.

A headmaster's annual report for the academic year 1967-1968. Contents: Numbers; Staff; Academic; Faculty Reports; Chapel; Library; Drama; Societies; C.C.F.; Health; Accommodation; Old Oakhamians; General. Attached is the Ruddles House report (appendix A). Eighteen pages A to R.

A prospectus promoting studying at Oakham School in 1922. Contents: Trustees & Staff; Brief History of the School; Subjects of Instructions; Boarding Houses; Buildings; Scale of Fees; Health; Scholarships and Exhibitions.

Part of a prospectus promoting studying at Oakham School in 1929. Contents: Trustees & Staff; Brief History of the School.

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).

A prospectus promoting studying at Oakham School in 1897. 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.

Documents relating to the annual report to Trustees by the Headmaster Graham Smallbone, and a music report by Peter Witchell. Three pages A to C.

Notes from Graham Smallbone for the next Policy Meeting held on 21 October 1986, including comments on policies, school numbers, School campus and buildings, maintenance, OSEL and Appeals. Six pages A to F.

A letter (A) from Graham Smallbone, Headmaster, Simon Schanschieff, Chairman of Trustees, and Rev Terence Treanor, Honorary Secretary of the Old Oakhamian Club, to former pupils who were at Oakham during John Barber's years with the School regarding celebrating his eightieth birthday and the Barber Archives. Attached is a reply slip (B).

An edition of Matkin's almanack including a section on Oakham School on page 16.