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This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

This file focusses on Oakham School's teaching staff Code of Conduct.

A collection of photographs of the Barraclough Hall since its construction in 1946. Once a warehouse at the terminus of the Canal on Ashwell Road, later converted into stables, the Barraclough Hall was named in honour of Mrs Barraclough, benefactor to the school, and in memory of her late husband, Norman Barraclough (OO, 1883). At the west end was the stage and the theatre would seat about three hundred and fifty people. Other features included a traditional long hall, raked stage and Proscenium Arch. The opening ceremony took place on 20 June 1953.

This file focusses on writings by John Buchanan. Some items are articles, other items are his books.

This file focusses on material relating to Jon Wills' time at Oakham School as a pupil.

This series focuses on the Junior House/Chapmans pupils and staff since its opening in 1910. It first comprised the Junior Department with facilities for boys boarders and classrooms. The house was renamed Chapmans in September 1960, after Frank Emerson Chapman, first Housemaster of the Junior House; it became a Senior House. Most of the series is made of photographs, house photographs as well as more informal photographs.

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

This series focusses on the headmastership of Graham Smallbone (1985-1996) and contains items relating to the life at School in the 1980s and 1990s, its staff and pupils.