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This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.

Two letters (A and B) from Graham Smallbone, Headmaster, and John Buchanan and Rev Terence Treanor asking Old Oakhamians to support the construction of the new library as part of the 1993 Development Plan. One letter was sent to O.O. who left in 1965 or earlier; one letter was sent to O.O. who left in 1966 or later.

Seven letters regarding the opening of the Rutland Crown Court in Oakham Castle on 13 January 1992.

Three letters between the Headmaster Graham Smallbone and Mrs Vera Furner regarding the donation of O.O. Maurice Kingham's autograph book to the School in 1995.

A note from the Personal Assistant to the Headmaster to Graham Smallbone regarding a message from Mr Ronald Dudley on the Court opening, the performance of the choir and Sir John Owen's grandfather attending Oakham School.

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, Simon Schanschieff, Chairman of Trustees, and Rev Terence Treanor, Honorary Secretary of the Old Oakhamian Club, to former pupils who were at Oakham during John Barber's years with the School regarding celebrating his eightieth birthday and the Barber Archives. Attached is a reply slip (B).

A letter from the Headmaster Graham Smallbone to Mrs Vera Furner regarding the donation of Mr Maurice Kingham's Autigraph book.

A letter (A) from the Headmaster Graham Smallbone to be sent to Old Oakhamians after the Appeal launch. Attached are two lists (B and C) of recipients.

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.