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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.

An edition of Matkin's almanack including a section on Oakham School on page 16.

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

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.

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.

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.

The Old Oakhamian Magazine, published in 1972. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; Gordon Purdy; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Changes of Address; Masonic Lodge; Notices; Diary Dates; Golf. Fourteen double-pages A to N.

A bound copy of several Old Oakhamian Magazines from 1968 to 1973.

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

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.