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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.

A5 magazine named The Oakhamian, stappled; 33 pages; contents on the inside cover: School News, the Library, the Museum, Quinquennal Fetival - 1939, Debating Society, Music, Cricket v. Old Oakhamians, O.T.C., Scouts, the First Six Weeks, Swimming Sports, Football, War List, O.O. News

A5 magazine named The Oakhamian, stappled; 15 pages; contents on the inside cover: Roll of Honour, Editorial, School News, Music Notes, debating Society, Lectures, J.T.C., Scout Notes, Football, Hockey, Running, O.O. Notes, Correspondence

A5 magazine named The Oakhamian, stappled; 23 pages; contents on the inside cover: Roll of Honour, Editorial, School News, Labour, Library, Music Notes, J.T.C., A.T.C., Scout Notes, Captain Brassbound's Conversation, Swimming Sports, Football, Debating Society, O.O. Notes

The order of service from the event including hymns and readings.

A newspaper cutting discussing R.G.Bisseker who taught at Oakham School during World War One.

An order of service for the Remembrance Day Service in All Saints Church

A photo of the boys cricket team. Names on reverse.

A4 page, 'A wartime interlude' - a recollection by Philip Newell