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A letter from the Headmaster Richard Bull to Parents regarding guidelines when pupils have parties during term time, and future term dates.

A letter from the Headmaster Richard Bull to Parents regarding the dress code for the School photograph, the 1984 Ball and the new Activity Holidays brochure.

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 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.

This file focusses on various speeches given by John Buchanan during his headmastership and later. It is an almost complete collection of his sermons given at Oakham School since 1958.

This file focusses on photographs of Graham Smallbone, during his Headmastership (1985-1996) and various visits to the School in the 1980s and 1990s.

A staff handbook for the academic year 1995-1996. Fifty-three pages A to BA.

This file focusses on photographs and artwork of John Buchanan, during his Headmastership (1958-1977) and various visits to the School in the 1980s and 1990s.

This file focusses on various items relating to the history of Oakham School, its pupils and Old Boys, under the headmastership of Rev William Spicer Wood.

This file focusses on matters of the Parent/Teacher Committee during the headmastership of Richard Bull.