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This series focusses on the headmastership of Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

A note from George Finch, enclosing letters HEA/1/4/1/2.

This file focusses on letters and cards relating to Oakham School, sent/received under the headmastership of Rev Vere Hodge.

A letter to Philip Robson from Jeremy Tomlinson concerning the payment and donatations to the school coming from Buchanan's estate. Attached is a letter to Dalton's solicitors concerning the same topic.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

A letter from John Buckingham to Jon Wills regarding naming Deanscroft house photograph of summer 1963, enclosing list of names

A5 magazine named The Oakhamian, stappled; 35 pages; contents on the inside cover: Editorial, School News, Music Notes, Speech Day, Athletic Sports, O.T.C., the 17th Foot, Scout Notes, Cricket, O.O. News, Cambridge Letter, Acknowledgements

A5 magazine named The Oakhamian, stappled; 36 pages; contents on the inside cover: Editorial, School News, Music, Miss Harrison, School Societies, Sports, Greek tragedy & French Comedy, Shakespeare in Modern Dress, Swimming, O.T.C., Scouts, Two Poems, Cricket, O.O. News, Correspondence; with a photograph of the gate on Church Passage

A5 magazine named The Oakhamian, stappled; 27 pages; contents on the inside cover: School News, Swimming Sports, Stamp Club, Scout Notes, Cub Notes, H.M.S. Pinafore, Geography Society, Field Society, History Society, Musical Lecture, Staffa and Iona, Debating Society, Art Society, Bardell versus Pickwick, Fives, Railway Society, C.C.F., Shooting, Music Notes, Play Reading Society, Sparks from the Torch, the Model Club at Work, Rugby Football, Cricket, O.O. News, Corresondence; stamped "Chapmans"

A5 magazine named The Oakhamian, stappled; 40 pages; contents on the inside cover: School News, Speech Day, Music Notes, Elijah, C.C.F., Scout Notes, Cub Notes, Geography Society, the Museum, Photographic Society, Debating Society, Field Society, Railway Society, the Castertonn