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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.

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 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 series focuses on the Day boys of Clipsham, founded in 1997. The main items are house photographs and handbooks.

This sub-series focuses on the administration of Clipsham House.

A letter from Clipsham tutors - Lick Brown, Steve Glynn, David Harrow, Frank Hayes, Ann Lewis and Peter Witchell - to parents asking them to contribute to a present for Mike and Margaret Rochester, retiring at the end of the academic year in 2004.