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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.

A newspaper cutting from the Rutland Times of an article on Jim O'Kane, retiring after 33 years at Oakham School, and a photograph of the Lower School prizes winners at Speech Day.

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 Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

A letter ((A) from the Headmaster Richard Bull to the Editor of The Rutland Times regarding two inaccuracies in the account of Speech Day 1978, published on the front page of Issue no. 15. Enclosed is the article (B).