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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.

A letter from the Headmaster Graham Smallbone to T.M. Reay, Mrs Wheway, Roger Blackmore and the Housekeepers, containing the minutes of a meeting regarding OSEL, conferences and support to house staff. Two pages A and B.

Four sample letters (A to D) from the Headmaster Graham Smallbone to be sent to potential donors to support the 1993 Development Plan.

An invitation from the Headmaster Graham Smallbone to Old Oakhamians to the launch of the Oakham '93 appeal, held in the QET on 17 April 1993.

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).

Four identical letters (A to D) from Headmaster Graham Smallbone and four other members of staff - Roger Blackmore, Nigel Webb, John Buchanan and Rev Terence Treanor- to Old Oakhamians. Attached is a mailing list (E).

A letter (A) from the Headmaster Graham Smallbone to be sent to Old Oakhamians who attended the OO Dinner regarding their contribution to the 1993 Development Plan. Attached is a list (B) of recipients.