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.

An almost complete collection of the Old Oakhamian magazines dating from 1897, until 2002. From that date, the Old Oakhamian has been included into the Oakhamian Magazine..

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).

This file focusses on arrangements and administration for C.C.F. inspections since the 1970s.

A letter (A) from Graham Smallbone, Headmaster, and Roger Blackmore, Joint Secretary of the the Old Oakhamian Club, inviting Old Oakhamians to a special reunion. Attached is a reply slip (B).

A bound copy of several Old Oakhamian Magazines from 1994 to 2002.

The Old Oakhamian Magazine, published in Autumn 1998. Contents: Team of the Year; News of; Goodbye; Deanscroft/Haywoods 50th Anniversary; All Your Yesterdays; O.O. Sports; Obituaries; School Sport.

The Old Oakhamian Magazine, published in Summer 2000. Contents: Reunion of '80-'85; The Torch is on its Way; Paris Dinner; News of; A Century of Sporting Achievement; Roll of honour; Births, Marriages & Deaths; The Millennium Chapel Appeal; Obituaries; Database and Website.

The Old Oakhamian Magazine, published in Summer 2001. Contents: The Return of The Torch; A Gala Evening for Macbeth; Unbeaten XVs Dinner; News of; Births, Marriages & Deaths; Obituaries; All Our Yesterdays; Sports News; Dublin Dinner. Four double-pages A to D.

A seating plan for the H.M. Armed Forces reunion lunch on 5 May 2006, with some hand-written amendments.