A letter from the Headmaster, John Buchanan, to Parents regarding the events of the Spring term 1958, including the hockey season, the works on the Sargant Laboratories, the raising of the minimum age of boarding and Speech Day. Two pages A and B.

A letter from the Headmaster Richard Bull and the Chairman of Trustees T.C.S. Haywood to Parents regarding the building of a new Biology Block, including plans, and the pre-payment of fees scheme III. Two pages A and B.

A letter from Richard Demarco to Graham and Dorothea Smallbone regarding his visiting the Queen Elizabeth Theatre and the performance of the Jerwood Players in 1995.

This file focusses on letters sent by Headmaster Richard Bull during his headmastership (1978-1984). The bulk of the collection is made of letters sent to Parents.

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.

This series focusses on the headmastership of Rev William Spicer Wood (1846-1875) and contains items created by the headmaster himself as well as items relating to the life at School in the mid-19th century.

An article written by former Headmaster John Buchanan in 1980, detailing the configuration of the School and the Technology block. Two pages A and B.

A programme for an amateur performance given by the students to celebrate the opening of the new buildings of Oakham Grammar School on 8 September 1858.

This file focusses on various items relating to the history of Oakham School, its pupils and Old Boys, under the headmastership of Rev William Spicer Wood.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).