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This series relates to various annual reports presented to the Trustees, including Headmaster's reports, Registrar's reports and Second Master's reports. The series spans over three Headmasters, John Buchanan, Richard Bull and Graham Smallbone.

A group of photographs, taken by the Photographic Society and David Morgan, of the Royal visit, C.C.F. training, boys walking on campus, the Baths and the archaeological dig on the Castle grounds.

The series contains negative files produced by Roger Blackmore, showing pupils, staff, school campus and buildings, drama productions, sports competitions and other activities.

The Old Oakhamian Magazine, published in 1955. Contents: Editorial; Annual General Meeting; Annual Dinner; Regional Meetings; O.O. Fund; The War Memorial Library; School News; O.O. Notes; Fr Louis Merton; Oakham, Uppingham and St Olave's; Engagements, Births, Marriages & Deaths; Obituaries; New Members; Changes of Address; Review - A Chindit Story; Notices; Golf. Ten double-pages A to J.

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 1962. Contents: Editorial; This Year's President; Annual General Meeting and O.O. Day; Annual Dinner; Regional Meetings; O.O. Fund; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part II; Notices; Stop Press; Golf. Twelve double-pages A to L.

The Old Oakhamian Magazine, published in 1963. Contents: Editorial; This Year's President; Annual General Meeting and O.O. Day; Annual Dinner; Regional Meetings; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part III; Notices; Golf. Eleven double-pages A to K.

The Old Oakhamian Magazine, published in 1964. Contents: Editorial; This Year's President; Annual General Meeting and O.O. Day; Annual Dinner; Regional Meetings; Development Campaign; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part IV; Notices; Golf. Fourteen double-pages A to N.

The Old Oakhamian Magazine, published in 1970. Contents: Editorial; The Appeal - What Now?; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; School News; The Shakespeare Centre; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address List Part V; Masonic Lodge; Notices; Rugby Fixtures; Diary Dates; Golf. Fourteen double-pages A to N.

The Old Oakhamian Magazine, published in 1984. Contents: Editorial; This Year's President; Annual Dinner; Annual General Meeting and O.O. Day; Regional Meetings; Oakham's Earliest Headmasters; A Breathing Space for Independent Schools?; North to the Future; Quatercentenary Appeal; Major Events 1984; School News; O.O. News; Engagements, Marriages, Births & Deaths; Obituaries; New Members; Address Changes; Golf; Rifle Club; Masonic Lodge; Notices; School Shop/Club Colours; Rugby Fixtures and Diary Dates; A Statistical History of Oakham School 1st XI Cricket; Centre Section - Oakham School Campus 1984. Eighteen double-pages A to R.