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The Old Oakhamian Magazine, published in 1953. Contents: Editorial; Annual General Meeting; Dinner; Regional Meetings; War Memorial Fund; O.O. Fund; The Barraclough Hall; School News; Olympic Games, 1952; O.O. Notes; Engagements, Births, Marriages & Deaths; Obituaries; New Members; Changes of Address; Father Douglass of Behala; Tweakerisms; Notices; Correspondence; Golf. Eight double-pages A to H.

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.

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

This file focusses on various prospectuses published under the headmastership of Walter Lee Sargant in the early 20th century.

A prospectus promoting studying at Oakham School in 1903, with illustrations. Contents: Brief History; Subjects of Instruction; Boarding Houses; Health; Games; Holidays.

This focusses on photographs of the Headmaster, Walter Lee Sargant, as well as various photographs of Oakham town in the early 20th century.