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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.

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

A photograph of Oakham School staff in the late 1950s/early 1960s, under Headmaster John Buchanan.

A negative of the 'Big Four' standing outside the War memorial Library in 1966.

A photograph of Geoffrey Liebert, Pat Liebert and john Moore. Date is unknown.

A photograph of the boys in School House in the academic year 1952-1953 under the Housemaster John Moore.

A photograph of the boys in School House in the academic year 1945-1946 under the Headmaster G. Talbot Griffith.

The Oakhamian Magazine, recording the Winter term 1965 (published in Spring term 1966). Contents: Editorial; School News; Avete; Term's Eye View; College House; Drama; Music Notes; Opinion Poll; Saas Fee 1966; Geographical Field Study; Societies; English and Universities at Oakham; Literary; We Pay our Respects to; Games; The Combined Cadet Force; Letters to the Editor; O.O. News; Valete.

The Oakhamian Magazine, recording the Spring term 1966 (published in Summer term 1966). Contents: Editorial; School News; Avete; Term's Eye View; RFD, GRL, JM; Drama; Music; Around the Societies; Oakham Through the Looking Glass; Letter from America; Literary; We Pay our Respects to; Face to Face; The Combined Cadet Force; Arduous Training; Shooting; Scouts; Games; O.O. News; Valete.