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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 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 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.

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.

A letter from the Acting Headmaster Michael Stevens to Parents regarding the term's sports achievements, Music concerts, Drama news and the influenza vaccination.

A letter from the Headmaster Richard Bull to John Barber regarding his arriving at Oakham School, and gratitude to staff and Old Oakhamians in his first term.

A letter from the Headmaster, John Buchanan, to Old Oakhamians regarding the upcoming reunion for the Talbot Griffith generation on 16 July 1972.

A letter from the Headmaster, John Buchanan, to Parents regarding the events of the Spring term 1958, including the hockey season, the works on the Sargant Laboratories, the raising of the minimum age of boarding and Speech Day. Two pages A and B.

A letter from the Headmaster, John Buchanan, to Sandy Thompson regarding his generous gift of equipment for the Photographic Society and the visit of the Continuation Manager for the Development Campaign.

A letter from the Headmaster, John Buchanan, to Sandy Thompson regarding Oxbridge results in 1967 and holding a house for Nigel Webb in the Kilburn Yard.