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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.

The Old Oakhamian Magazine, published in 1966. Contents: Editorial; This Year's President; Annual General Meeting and O.O. Day; Annual Dinner; Regional Meetings; School News; O.O. News; R.F.D.; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part I; Masonic Lodge; Notices; Correspondence; Diary Dates; Seven-a-Sides; Golf. Thirteen double-pages A to M.

A bound copy of several Old Oakhamian Magazines from 1960 to 1967.

A salaries cash book, recording salary, payments, tax, and lunch for teaching staff, admin staff and matrons, from May 1963 to November 1965.

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).

Two bound copies of several Oakhamian Magazines from 1960 to 1963. Item A has a black cover; item B has a brown cover.

A bound copy of several Old Oakhamian Magazines from 1994 to 2002.

An account book recording staff wages and salaries, income and expenditure from Christmas term 1945 to Summer term 1949.

An account book recording pupils' fees, staff wages, various income and expenditure from Summer term 1930 to Easter term 1939.

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