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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.

This series focusses on recreational events for staff by the Common Room and by Oakham School Enterprise Ltd, such as Christmas Parties, Burns Night and swimming pool sessions, from 2005.

Internal email correspondence regarding the organisation of the first Christmas Party in 2005, discussing matters such as date, menu, venue, guest list, costs, and entertainment. Thirty-nine pages A to AM.

A collection of invitation and programme for the C.C.F. Biennial Inspection on 5 May 2006, as well as correspondence from the Foundation to guests, and letters from guests to the School regarding the event.

A letter from Bee [?] to the Headmaster Dr Joe Spence thanking him for a wonderful day at the C.C.F. Inspection on 5 May 2006, enjoying in particular the Merlin helicopter. With a drawing of an helicopter by Alec and James [?].

A letter from Robert Gregory to the Headmaster Dr Joe Spence thanking him for an enjoyable day at the C.C.F. Biennial Inspection and Reunion on 5 May 2006.

A letter from Max Heron to the Headmaster Dr Joe Spence congratulating him on the C.C.F. Biennial Inspection and Reunion on 5 May 2006.

A letter from Air Vice Marshal Anthony J. Stables thanking Martin Minshall, Director of the Foundation, for the memorable day that was the C.C.F. Inspection on 5 May 2006.

A letter from Squadron Leader K.E. Skinner to the Headmaster Dr Joe Spence congratulating him and Oakham School staff for an exceptional C.C.F. Biennial Inspection on 5 May 2006.

A letter from Air Vice-Marshal Simon Bryant thanking the Headmaster Dr Joe Spence for an enjoyable day at the C.C.F. Biennial Inspection on 5 May 2006.