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.

A collection of material which focuses the school accounts and financial procedures over the years. This includes information on general accounts, pupil fees, committee minutes, staff wages, legal proceedings, and guidance policies for staff.

Old Oakhamian Calendar, published in 1899. Cover with contents: Editorial; The Old Oakhamian Club; Members of the Old Oakhamian Club - 1898; Old Oakhamian Notes; The Old Oakhamian Dinner - 1898; The Oakham School Register. This is the first issue of the Old Oakhamian Magazine, recording news of the O.O. Club and former pupils.

A bound copy of several Old Oakhamian Magazines from 1899 to 1913.

Old Oakhamian Calendar, published in 1902. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1902; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts. Six double-pages A to F.

A bound copy of several Oakhamian Magazines from 1902 to 1910.

Old Oakhamian Calendar, published in 1907. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1907; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts. A note on the inside cover from John Barber regarding the years of publication of this magazine. Six double-pages A to F.

Old Oakhamian Calendar, published in 1910. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1910; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts. Seven double-pages A to G.

Old Oakhamian Calendar, published in 1913. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1913; Old Oakhamian Notes; Old Boys' Matches; O.O. Club Accounts.

A bound copy of several Oakhamian Magazines from 1911 to 1919.