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A letter from the Headmaster Graham Smallbone to Bryan Waites at the Rutland County Museum regarding celebrating the 450th anniversary of the birth of Archdeacon Robert Johnson and an article in This England.

A letter from the Acting Headmaster Michael Stevens to Parents regarding School fees.

A letter from the Acting Headmaster Michael Stevens to Parents regarding the School rules on drinking for day pupils and boarders.

A letter from the Headmaster Graham Smallbone to Dermot Gilvary, Head of Drama, regarding some décor being nailed to the woodwork in the Shakespeare Centre and proper use of the building.

A letter from the Bursar Trevor Case to Michael Stevens regarding recommendations for Old School in 1985.

A note to the Headmaster Graham Smallbone regarding Michael Stevens suggesting asking John Barber about the frescoes.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

Four letters sent/ received by Joe Spence and Paul Spicer regarding the composition of 'A Living Stone' and the arrangements for the Rededication service in 2007.

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 the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.