This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

An almost complete collection of the Old Oakhamian magazines dating from 1897, until 2002. From that date, the Old Oakhamian has been included into the Oakhamian Magazine..

Old Oakhamian Calendar, published in 1924. Cover with contents: Editorial; List of Addresses of Members of the Old Oakhamian Club - 1924; Meeting of Old Oakhamian Club; Old Oakhamian Luncheon; A Letter from the Headmaster; Cambridge Letter; Officers' Training Corps; A Weekend in Africa; Births, Deaths and Marriages; Old Oakhamian Matches; School Staff - September 1924. Nine double-pages A to I.

Old Oakhamian Calendar, published in 1927. Cover with contents: Frontispiece; Editorial; Names and Addresses of Members of the Old Oakhamian Club; Annual Dinners; Presentation to Mr J.C. Clark; The Headmaster's Letter; Cambridge Letter; Review of School Games, 1924-1927; Mr J.C. Clark's Trip to Canada; Births, Deaths and Marriages; Old Oakhamian Notes; Cricket and Football Matches; School Staff - September 1927. Thirteen double-pages A to M.

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.

The Old Oakhamian Magazine, published in 1932. Contents: Annual Dinner; Cricket, Football and Fives; The Golfing Society; The School, 1931-1932; George; New Members; Births, Deaths and Marriages; Obituary; O.O. Notes; Notices; Football Fixtures, 1932-33. Two double-pages A and B.

The Old Oakhamian Magazine, published in 1933. Contents: Annual Dinner; Cricket and Football; The Golfing Society; The School, 1932-1933; Births, Deaths and Marriages; O.O. Notes; Notices; Football Fixtures, 1933-34. Two double-pages A and B.

The Old Oakhamian Magazine, published in 1934. Contents: Quinquennial Meeting; Annual Dinner; Cricket and Football; The Golfing Society; School Notes; Births, Deaths & Marriages; O.O. Notes; New Members; Notices; School Football Fixtures; Correspondence. Two pages A and B.

The Old Oakhamian Magazine, published in 1936. Contents: Annual Dinner; Old Oakhamian Fund; Cricket, Football and Golf; School Notes; Births, Marriages and Deaths; In Memoriam; Old Oakhamian Notes; Notices.