This collection charts the history and activities of the Old Oakhamian Club. It has excellent records of dinners and events thrown by the club such as reunions, international dinners and Oakham events. Most of the documents are administrative, but there are photographs and correspondence material too.

There are good records on the school's foundation and the club's golfing society. Most of the material has been produced by the Old Oakhamian club or the foundation. Thus, there is a good record of publications and marketing material relating to these events.

Issue of The Old Oakhamian Calendar. Contents: Editorial, Members of the Old Oakhamian Club 1910, Old Oakhamian Notes, Old Boys' Matches, O.O. Club Accounts; with hand-written notes on the Members list.

Issue no.3 of "The Old Oakhamian". Contents: Annual Dinner, Cricket and Football, The Golfing Society, The School 1932-1933, Births, Deaths and Marriages, O.O. Notes, Notices, Football Fixtures 1933-34; with a loose page: Changes of Address. Pages A to C.

A list of the Old Oakhamian Club members and their addresses from October 1933. Pages A and B.

Issue no. 5 of "The Old Oakhamian". Contents: Annual Dinner, Old Oakhamian Fund, Cricket, Football and Golf, School Notes, Births, Deaths and Marriages, O.O. Notes, New Members, Changes of Address, Notices, School Football Fixtures, Correspondence.

Issue of The Old Oakhamian Calendar. Contents: Editorial, Members of the Old Oakhamian Club 1910, Old Oakhamian Notes, Old Boys' Matches, O.O. Club Accounts; with hand-written notes on the Members list.

Issue of The Old Oakhamian Calendar. Contents: Editorial, Members of the Old Oakhamian Club 1913, Old Oakhamian Notes, Old Boys' Matches, O.O. Club Accounts.

Issue no.1 of "The Old Oakhamian". Contents: Annual Dinner, Cricket and Football, The Golfing Society, Cambridge University, O.O. Club, The School 1930-1931, Opening of the Pavilion, New Members and Changes of Address, Births, Marriages and Deaths, O.O. Notes, Notices; with a photograph of the Pavilion 1931 and a photograph of the School's 1st Xi v. Old Oakhamians. Pages numbered A to D

Issue no. 7 of "The Old Oakhamian". Contents: Annual Dinner, Old Oakhamian Fund, Cricket, Football & Golf, School Notes, Births, Marriages and Deaths, O.O. Notes, Notices, School Football Fixtures, Correspondence.

Issue no. 8 of "The Old Oakhamian". Contents: Editorial, Annual Dinner, Old Oakhamian Fund, Cricket, Football, Golf, School Notes, Old Oakhamian Notes, Births, Marriages & Deaths, Obituary, Correspondence, Notices, School Football Fixtures, New Members.