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This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

This series relates to College House, the pupils who lived there and the history of the building.
College House was built c.1320 and used to be a priest’s house for clergy sent to the town by Westminster Abbey. Oakham School bought College House from the Church in 1736. It served as the school’s Sanatorium until 1965, when College House was then converted into a boarding house for a dozen potential Oxbridge candidates.
In 1971, College House became the first girls’ boarding house. In 1982, it was converted to be used as a Seventh Form Study Centre.
Since 2007 College House has been converted into offices. The Foundation and Marketing moved in and the Senior Deputy Heads use the wing as their private residence. The Barber Rooms, housing the School Archives, opened in 2010 on the first floor and the Old Oakhamian Club is now on the ground floor.

This series contains various recording materials related to some years at Oakham School.

A collection related to the History of Oakham School since its foundation, including research on Headmasters, Masters and pupils, and articles and books published by Headmasters and teachers.

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.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

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 focusses on the headmastership of Francis Cecil Doherty (1929-1935) 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 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 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.