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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 Patrick Wilson to Stephen Kimbell asking for a small contribution to the 1993 Appeal. Three pages A to C.

A letter from Andrew to John Barber regarding his book "The Story of Oakham School" and sharing memories of his time at school as a pupil.

Two letter from Tony Earl congratulating John Barber on his book "The Story of Oakham School".

A letter from Peter North, Principal of Jesus College, Oxford, to John Barber regarding his book "The Story of Oakham School".

A letter from Geoffrey P. Lockwood to John Barber sharing memories on his time at school, prompted by an article in The Telegraph.

A letter from C.C. Love to John Barber regarding "The Story of Oakham School" and "Operation Oakham", and sharing some memories of his time at school.

A letter from Mark Jenkins to John Barber, prompted by an article in the Rutland Journal advertising the publication of "The Story of Oakham School" and sharing memories of the digging of the Roman Villa at Great Casterton while at school.

A letter from Edward Simpson congratulating John Barber on the publication of "The Story of Oakham School" and sharing his memories of the school during the Second World War.

A letter from OO John Ingram ('32) congratulating John Barber on his book "The Story of Oakham School" and sharing some memories of his time as a pupil.