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This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This file focusses on roll call lists from the early 20th century, under the headmastership of Walter Lee Sargant.

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

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

Old Oakhamian Calendar, published in 1913. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1913; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts.

Old Oakhamian Calendar, published in 1930. Cover with contents: Frontispiece; Editorial; Names and Addresses of Members; Annual Dinners; Headmaster's Letter; Mr J. Story's Letter; Quinquennial Luncheon and Meeting; Resignation of Mr W.L. Sargant - An Appreciation; The Captain of the Ship; Presentation to Mr W.L. Sargant; Cambridge Letter; The Book of Oakham School and The Register; Births, Marriages and Deaths; Cricket, Football and Shooting Matches; The Golfing Society; Club Notices; School Staff. Eighteen double-pages A to R.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

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

The Old Oakhamian Magazine, published in 1961. Contents: Editorial; This Year's President; Annual General Meeting; Annual Dinner; Regional Meetings; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part I; Notices; Golf; Stop Press. Twelve double-pages A to L.

The Old Oakhamian Magazine, published in 1968. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; O.O. News; K.R.B.; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part III; Masonic Lodge; Notices; Diary Dates; Golf. Fourteen double-pages A to N.