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A prospectus promoting studying at Oakham School in 1922. Contents: Trustees & Staff; Brief History of the School; Subjects of Instructions; Boarding Houses; Buildings; Scale of Fees; Health; Scholarships and Exhibitions.

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 bound copy of several Oakhamian Magazines from 1911 to 1919.

Oakham School Magazine, recording the Winter term 1910 (published in Spring term 1911). Contents: School Notes; Officers' Training Corps; A Son of Empire; Mr. A.C. Johnson, Late Hereditary Trustee; The Concert; Rome; Wild Nature's Way; Caravan and Camera; Football; Correspondence. Seven double-pages A to G.

A bound copy of several Oakhamian Magazines from 1935 to 1937.

A book compiling the minutes of the Trustees' Financial Committee meetings.

A letter from O.O. Lt Col Jim Fife to the Headmaster Graham Smallbone regarding the frescoes in Old School.

A brief history of School House written by Jim O'Kane. Four double-pages A to D.

Printed Powerpoint slides from a presentation on the centenary of Chapmans. Includes information on the school's founding, images of various school buildings from different times, campus maps and pupils; a history of Junior House/Chapmans House; and a list of Housemasters. Thirty-four pages A to AG.

A list of Trustees, Old Oakhamians, Parents of present boys and Personal friends who raised the Sargant Presentation Fund in order that an organ might be placed in Oakham School Memorial Chapel. The book was presented to Walter Lee Sargant by Colonel Sir Herbert Bryan on 26 July 1930 when the organ was dedicated. Thirteen pages A to M.