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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; 32 pages; contents on the inside cover: Editorial, School Notes, F.C.D., the Chapel, the Library, Careeres, the Photographic club, Philatelic Society, Debating Society, Reading Society, Music Notes, Art, Scout Notes, O.T.C., Cricket, Football, Swimming Sports, Golf Notes, Contributions, Cambridge Letter, London Letter, O.O. Notes, Acknowledgments

A5 magazine named The Oakhamian, stappled; 27 pages; contents on the inside cover: School News, Music Notes, Philatelic Society, Debating Society, Reading Society, School group of National Savings Association, O.T.C., Scout Notes, Swimming Notes, Cricket, Football, W.H. Weston of Northampton, Boxing, O.O. News, Correspondence, Acknowledgements

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

A5 magazine named The Oakhamian, stappled; 24 pages; contents on the inside cover: School News, J.T.C., Scout Notes, Music Notes, Mendelssohn's "St. Paul", Macbeth, Stamp Club, the geography Society, Speech Day, Boxing, Junior Sports, Athletics, Cricket, O.O. News, Football Fixtures

A5 magazine named The Oakhamian, stappled; 20 pages; contents on the inside cover: School News, the Photographic Society, the Debating Society, the Geography Society, Valete, School Officials, Avete, Chess Club, Oakham School Summer Concert, Cricket, Swimming Sports, Stamp Club, Scout Notes, Cubs, J.T.C., Certificate A and National Service, Music Notes, Railway Society, History Society, Hodge Wing Christmas Entertainment, Hockey, Rugby Football, Sparks from the Torch, O.P.R.S., Obituary, O.O. News, Correspondence; "D.J. Stocks/Junior House/Oakham/Rutland/or "Tealby"/42 Park Ave/Grimsby/Lincs" hand-written on the cover

A5 magazine named The Oakhamian, stappled; 20 pages; contents on the inside cover: School News, O.S.P.G. Entertainment, Chess Club, Handel's Messiah, Nativity Play, Music Notes, the Debatng Society, Stamp Club, Scout Notes, Cub Notes, J.T.C., Railway Society, Hockey, Cricket Fixtures, Rugby Football, the Steeplechase, Fifty Years Ago, the Geography Society, Sparks from the Torch, O.P.R.S., History Society, O.O. News, Cambridge Letter; stamped "Chapmans"

A5 magazine named The Oakhamian, stappled; 27 pages; contents on the inside cover: School News, Francis Joseph Hill, Music Notes, Rialway Society, Steeplechase, Athletic Records, Running Matches, Debating Society, Field Society, C.C.F., Scout Notes, Cub Notes, Boxing Match, Play Reading Society, Under 14, Fives, Geography Society, Twelfth Night, History Society, Museum, Art Society, Hockey, Team Characters, House Matches, Cricket Fixtures, O.O. News; "Stocks/Junior House/Oakham/Rutland/or/42 Park Ave/Grimaby/Lincs", "Quasi Cursores", "64th Edition" hand-written on the cover