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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.

A letter from O.O. J.A.S. Taylor to Brian Welford regarding his sporting career and some school memories; enclosed are photocopies of pages from Mr Taylor's scrapbook containing cuttings on his rugby career in the 1930s. Nine pages A to I.

This series focusses on documents relating to Brian Welford' career at Oakham School as Master-in-charge of Rugby in the 1970s and 1980s. Also contains documents relating to the history of rugby and Old Oakhamians, kept by Mr Welford in his personal files.

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.

Two letters (A and B) to Roger Blackmore, new Chairman of the Holiday Lettings Committee, and to Nigel Webb, member of the Committee, regarding the new company and their new roles.

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.

A letter from john Barber to Brian Welford regarding an Old Oakhamian, Radu Nicolas Tabacavici ('31) who played in the 1st XV.

This file focusses on letters received by Brian Welford regarding rugby matches and his career as Master-in-charge of Rugby.

A letter from John Buchanan to Brian Welford congratulating him on the win against Uppingham and reflecting on Mr Welford's career as Rugby coach and the team's results.

A letter from Graham Smallbone, Headmaster, to R.M.P. regarding the accommodation for the Australian Gap Year students and their role within the school. Two pages numbered A and B.