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.

Two photographs of the boys in School House in 1905, under the Housemaster J.C. Clark. The photographs A and B are taken from different angles.

Research material on some soldiers and their family, most notably the Neilson brothers and the Sills family.

A collection of material which focuses on Old Oakhamians who fell in the First World War, containing personal and family items and research.

This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

A letter from Colin Edgar to Dr Joe Spence, Headmaster, enclosing "The Humf Letters".
"The Humf Letters" is a work by Colin Edgar, compiling letters sent by Lt. Douglas Herbert Washington Humfrey to Betty Dawes from the front during the First World War.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

Photocopies of various research resources on John Woodall Marshall from Ancestry, Rutland Remembers, Graves Registration Report Form, The London Gazette, including two print outs of photographs, presented by Michael Hawker, archaeologist Leicester University. Items numbered A to P.

An album containing photographs of the O.T.C. and C.C.F. at Oakham School. Some names are written next to the corresponding photographs. Topics include inspections, First World War Cuttings, Jubilee Parades, Armistice Day, Drums, Proclamation of King George VI, demonstrations of arms, letters and newspaper clippings.

Photographs and documents relating to Launcelot John Austen Dewar and his brother David Dewar.