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 letters relating to OSEL courses, Activity Holidays and events in the 1980s.

A red folder containing financial records and accounts of Oakham School Enterprises Ltd activities and minor events from 1982 to 1991.

A collection of reports and financial statements, and letters, related to the activities of Oakham School Enterprises Ltd (OSEL), spanning from 1978 to 1995.

A draft report and financial statement on Oakham School Enterprises Ltd activities; including balances, funds, loss and profits. Ten pages A to J.

A draft report and financial statement on Oakham School Enterprises Ltd activities; including balances, funds, loss and profits. Ten pages A to J.

A balance sheet on Oakham School Enterprises Ltd activities for the year ended 31 August 1995.

A green minute book recording minutes of working party meetings and general meetings of the Oakham School Foundation from the 2000s.

The Oakhamian Magazine, recording the Winter term 1933 (published in Spring term 1934). Contents: Editorial; School Notes; School Officials; Avete and Valete; The Swimming Bath; The Chapel; The Library; Careers; End of Term Concert; Lectures; The Rivals; Debating Society; Philatelic Society; Reading Society; Photographic Society; Scout Notes; The Shepherds' Play; O.T.C.; Shooting Notes; Fives Notes; Athletics; Poems; The term's Howlers; A Banner with a Strange Device; Cambridge Letter; O.O. News; Correspondence; Acknowledgments; Games Committee Balance Sheet. Nine double-pages A to I.

The Oakhamian Magazine, recording the Winter term 1930 (published in Spring term 1931). It is the 47th year of the School Magazine. Contents: Editorial; School Notes; Athletics; Football; Napoleon in our Midst; Our Village; Roots in the Soil; Motion; Requiem; The Study Wireless Set; O.T.C. Notes; Cambridge Letter; O.O. Notes; Acknowledgements; Correspondence; Games Committee - Balance Sheet for 1930. The name 'Worthington' is hand-written on the cover. Seven double-pages A to G.