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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 Richard Bull to Michael Stevens, Patrick Wilson and Housemasters regarding recommendations for the Anderson Awards.

A letter from the Headmaster Designate Henry Price to Parents regarding Sports Day and Speech Day in Summer term 2021.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Summer term 1996. Contents: Activities; Beef and BSE; Reports for Parents; Carol Service for Parents; Two Special Pleas; Changes of Staff. Two pages A and 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.

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 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 Graham Smallbone to Parents reviewing the Winter term 1992. Contents: The Future; Examination fees; Choral Society performance; Rutland - A Visitor's Guide; Three Special Requests; Responsibility for each other. Two pages A and B.

This file focusses on letters sent/received by John Buchanan, chiefly during his headmastership (1958-1977).