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A collection of material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.

A collection of photographs and artworks of the school campus and buildings, and pupils and staff.

There is one series dedicated to a large collection of photographic negatives which show the campus, daily life at school, and special events. These cover the period 1978 - 1988.

One series focus on the frescoes painted by Mary Sargant Florence in Old School and is rich in research about the frescoes and the artist.

An internal note from Rev John Darrall to Graham Smallbone, Rev Terence Treanor and Roger Blackmore regarding donations of chalices and ciboria to the Chapel.

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).

Two letters between Roger Blackmore and Michael de Grey Following the national Youth Chamber Orchestra's stay at Oakham School in August 1993.

A letter from Roger Blackmore to Michael de Grey regarding the National Youth Camber Orchestra staying at Oakham School.

A group of faxes and letter between Roger Blackmore and Michael de Grey.

A memo from Roger Blackmore regarding accommodation for the National Youth Chamber Orchestra in August 1993.

A note from Roger Blackmore to Rev John Darrall regarding the National Youth Chamber Orchestra using the Chapel in August 1993.

A letter from Roger Blackmore to Michael de Grey regarding the arrangements for the stay of the national Youth Chamber Orchestra at Oakham School in August, including numbers and costs.