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A prospectus (A) promoting studying at Oakham School in 1935. Contents: Trustees; Staff; Admission; Work; Fees; Optional Payments; Absence & Remission of Fees; Health; Entrance Scholarships; Other Scholarships & Exhibitions; Buildings; Boarding Houses; Holidays & Hours; Games & Hobbies; School Societies; Expenses; Clothes List. Enclosed are corrections to prospectus (B), and a form of application for admission (C).

A prospectus promoting studying at Oakham School in 1943. 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; J.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. Six double-pages A to F. Enclosed is a list of Trustees and Staff (G).

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.

A calendar of events in the Spring term 1949. Hand-written note on the cover reads 'Best wishes, JM'. Three double-pages A to C.

The Oakhamian Magazine, recording the Spring term 1963 (published in Summer term 1963). Contents: Editorial; School News; O.O. News; Avete; Speech Day; Societies; Music; Retreat - 1963; Comment; Face to Face no.2; Arduous Training 1963; The Combined Cadet Force; Scout Notes; Games; Letters to the Editor; Valete. Fourteen double-pages A to N.

A photograph of Oakham School staff in the academic year 1963-1964, under Headmaster John Buchanan.

Two lists of Commanding Officers and Officers of the O.T.C., J.T.C and C.C.F. since 1910, with names, ranks, and dates. Two pages A and B.

A photograph of the boys in School House in the academic year 1947-1948 under the Housemaster John Moore.

A photograph of the boys in School House in the academic year 1951-1952 under the Housemaster John Moore.