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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.

Two newspaper articles from the Leicester Mercury and The times reporting on Zhanna Lazhevskaya winning the first Chess Scholarship at Oakham School in 1998.

Press cuttings from Leicester Mercury regarding O.O. Frank Jerwood, former School Chaplain, retiring from Burton Overy rectory in 1957.

A press cutting from the Leicester Mercury regarding the daily life at Oakham School in the early 19th century and the publication of "The Story of Oakham School" by John Barber.

This sub-series focusses on press cuttings, magazines and other publications reporting on chess tournaments at Oakham School, on Oakham School Chess team competing in National Championships, and the development of chess at Oakham School.

This file focusses on various publication, mostly newspaper cuttings, related to the frescoes in Old School and the painter Mary Sargant Florence and post-medieval mural painting. This file is from the year 1993.

A group of press cuttings published in various local newspaper advertising the publication of John Barber's "The Story of Oakham School".

This sub-series relates to the history of Old School, oldest building of Oakham School, in Cutts Close park. It is made of a collection of photographs and art work; of newspaper cuttings and letters, mostly relating to the debate concerning the refurbishment of the building and preserving the frescoes painted by Mary Sargant Florence.

News paper cutting from the Leicester Mercury reporting on the debate concerning the frescoes in Old School.

Newspaper cuttings printed on one page reporting on the 1979 rugby visit from Japan School to Oakham School.