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A prospectus promoting studying at Oakham School in 1942. 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 is modifications to the clothes list due to Rationing in July 1941 (J).

A confirmation form filled in by Lucy Clewes-Garner, with information on her age, house, tutor, baptism, address and dates of meetings and visits for the candidates' preparation.

A copy of the portrait of Headmaster Nigel Lashbrook, painted by O.O. Rebecca Haley ('17). The original painting was presented on his last Speech Day.

A policy on the aims of Oakham School, written by the Headmaster Nigel Lashbrook in 2018. Two pages A and B.

The Old Oakhamian Magazine, published in 1973. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; H.J.C.; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Changes of Address; Masonic Lodge; Notices; Diary Dates; Rugby Fixtures; Golf. Fourteen double-pages A to N.

Order of service for the Jerwoods Carol Service in Peterborough Cathedral on 15 December 2009.

A roll call for School House, Mr. Scriven's, Mr Williams', Bank House and the Day Boys in Winter term 1887.

A bound copy of several Oakhamian Magazines from 1886 to 1893.

A bound copy of several Old Oakhamian Magazines from 1980 to 1984.

A photograph of Tim Shaw batting and David Webb fielding for the School's 1st XI. Date is estimated in the early to mid 1980s.