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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 Dr John Doncaster (1808-1846) and contains items created by the headmaster himself as well as items relating to the life at School in the early 19th century and Old Oakhamians, in particular James and Augustus Padley.

A letter from Dr John Doncaster to J.S.Padley regarding his son's elevation into the senior class in 1843.

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

This file focusses on letter sent by Dr John Doncaster, Headmaster of Oakham School, regarding some pupils and staff matters. File dates from the first half of the 19th century.