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.

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..

A menu for Buchanans and Haywoods Sixth Form Guest Night held on 22 January 2011 in the Barraclough. With signature of some of the attendees.

A group of photographs of various house events, such as Christmas celebrations, take away night, cooking, barbecues with the day boys, fancy dress and themed evenings.

A letter from Roger Blackmore to Alan Grieve responding to the memorandum AB/26/13/21 and giving feedback from an OO Committee meeting regarding the Dinner on 24 November.

A memorandum from Alan Grieve to Roger Blackmore confirming the arrangements for the OO Dinner.

A letter from Alan Grieve to Roger Blackmore commenting on a dinner, probably part of the Quatercentenary celebrations. Two pages A and B.

A letter from Roger Blackmore to Alan Grieve regarding a card to be sent to all Old Oakhamians and the catering arrangement for the OO Dinner.

A scrapbook compiled by John Barber from 1954 to 1979 and by Terence Treanor from 1979 to 1994, presented to the O.O. Club by C.H. Falconer. The album contains photographs of and newspaper cuttings related to O.O. Club events and Old Okahmians, their lives at school and after.

A menu for the Oakham School Rifle Club's Ashburton Celebration dinner on 6 December 1975.