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A letter from former Headmaster Walter Lee Sargant to Skevington regarding the latter's family, his brother, the death of miss Harrison and Sargant's plans.

This file focusses on photographs and drawing dating back from the Headmastership of Rev Edward Vere Hodge and includes photographs of his wife, the whole School, and various groups of pupils and visitors.

This file focusses on letters written or received by Walter Lee Sargant.

This file focusses on letters received/sent by the Headmaster Tony Little during his headmastership (1996-2002).

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 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.

An edition of Matkin's almanack including a section on Oakham School on page 16.

An almost complete collection of Oakham School magazines dating from 1884. Some editions are available as individuals whilst others can be found in larger bound volumes. There is also a collection of the Old Oakhamian magazine which is a separate school magazine for Old Oakhamians and their news.

This magazine covers all aspects of school life. Sporting, academic, and artistic achievements of the pupils are celebrated alongside news updates from various departments. In later issues, c. 1980s, houses are given space to announce news and in house achievements.

Sporting records are a key component of the magazine since its inception and there are accounts of matches (including scores and teams) in each edition. Again, since the 1980s, focus has shifted to also include all of the teams that compete for the school, instead of just focusing on the A team.

Images and photographs start to appear in the magazines from the 1970s and the magazine was first printed fully in colour in the 1990s.

Photo albums and scrapbooks compiled by members of staff throughout the years.

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.