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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.

Extract from a 1940 prospectus, published in the Old Oakhamian Magazine. Content: Size; Staff; Fees; Curriculum; Timetable; Diet & Tuck boxes; Games; Activities outside the classroom; Day Boys. Three pages A to C.

A5 magazine named The Oakhamian, stappled; 18 pages; contents on the inside cover: Roll of Honour, Editorial, School Notes, Speech Day, Music, O.T.C., Boxing, Sports, Cricket, O.O. News; stamped "Chapmans"

A5 magazine named The Oakhamian, stappled; 18 pages; contents on the inside cover: Roll of Honour, Editorial, School News, Mrs. Sweatman, George Hetterley, Library, Music Notes, Scout Notes, J.T.C., A.T.C., The Hands of God, Football, Hockey, Running, Boxing, Cricket Fixtures, O.O. Notes

A5 magazine named The Oakhamian, stappled; 15 pages; contents on the inside cover: Roll of Honour, Editorial, School News, Library, Tobias and the Angel, Music Notes, J.T.C., A.T.C., Scout Notes, Swimming Sports, Football, O.O. Notes; stamped "Chapmans"

A5 magazine named The Oakhamian, stappled; 16 pages; contents on the inside cover: Roll of Honour, School News, Speech Day, J.T.C., A.T.C., Scout Notes, Boxing, Music Notes, Mr. and Mrs. F.J. Hill, Miss Margaret Harrison, Library, Sports, Cricket, O.O. Notes