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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 file focusses on various speeches given by John Buchannan during his headmastership and later. The bulk of the file is an almost complete collection of his Speech Day speeches.

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.

This series focuses on a large range of services held in the School Chapel, such as memorial services, confirmation and baptism services, carol services, weddings, and the weekly and Sunday services attended by pupils. Most of the items are orders of services.

A wooden shield awarded by Rotary Club of Rutland at the Rutland Debating Festival in memory of P.P. 'Pop' Westmoreland. The shield has one central medallion and nineteen small metal medallions, nine of which are engraved with the wining school and year. Oakham School won in 1987, in 1992 and in 1995. Other winners are Uppingham Community College, Uppingham School, Vale of Catmose College and Casterton Community College.

This file focusses on letters received/sent by the Headmaster Graham Smallbone during his headmastership (1985-1996).

A photocopy of 1753 edition of "The Statues and Ordinances" of Robert Johnson, Archdeacon of Leicester, for the ordering, governing and maintaining of his Schools and Hospitals of Christ in Oakham and Uppingham in the county of Rutland, from 24 July 1625. On the last page is an account for the yearly rental of the estates belonging to both Oakham and Uppingham Schools from 11th October 1792. Pages are numbered A to M.

A list of the perpetual and elective Governors of the Schools and Hospitals of Oakham and Uppingham in 1586, hand-written.

A research booklet on the History of Oakham and Uppingham Schools by P. Wilkinson, as part of a special study at Coventry College Of Education.

A press cutting regarding two new publications telling the story of Oakham and Uppingham Schools to celebrate the 400th anniversary of their foundation.