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A collection of documents, mostly photographs, of the boarding house Haywoods on Kilburn Road, next to Chapmans. This new house was named after Colonel Tom Haywood, former Trustee. The boys previously in residence in Deanscroft moved into their new house in September 1989.

A speech given by Headmaster John Buchanan on Speech Day 1965, paying tribute to the new Chairman, Thomas Haywood, discussing three innovations to the education at Oakham School - a small Sixth Form house, the building of a Technology Department, and the establishments of setting by subjects and tutors, and sporting achievements. The speech is typed, with hand-written notations. Six pages A to F.

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 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.

This file focusses on photographs of Haywoods, a boarding house for boys, since its construction in 1988.

This file contains photographs owned by Rev Terence Treanor on various topics: House photographs, Sports team and school events and dinners.