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This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

This series focusses on the headmastership of Rev Edward Vere Hodge (1879-1902) and contains items relating to the life at School in the late19th century, its staff and pupils. The series contains some of the earliest photographs of Oakham School's collection.

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 series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

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 from the Headmaster Tony Little to Parents reviewing events of Spring term 2000. Contents: School rules; Music, Drama; Debating; Physics Olympiad; Sports achievements; Future dates.

A letter from the Headmaster Tony Little to Parents regarding a review of the Summer term 2001. Contents: Speech Day; Sporting achievements; Trips; Examinations results; Curriculum and Subject choices; Changes of Staff; Beginning of term dates; Dates further into the future.

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).

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.