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

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, John Buchanan, to C.H. Gadney, Chairman of the East India, Sports & Public Schools Club, regarding the creation of the Club, nominating one member of the Club to represent the School, and thanking him for his help with the Speech Day Visitor.

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.

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).

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

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

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.