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The Oakhamian Magazine, recording the Winter term 2000. Contents: Editorial; Chapel; OSCA; Oakham School Fitness Centre; Staff News; Interview with the Headmaster; 1000th Gold Awards Celebration; Drama and Music; Art, Design & Technology; Expeditions and Trips; Sport; House Reports.

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 contains various photographs of School House and Old Hall throughout the years.

A list of School buildings and their dates of construction and contractors compiled by R.E.M. Thomas, School Marshal, and other town buildings. Two pages A and B.

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.