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This collection covers the multitude of sports that pupils can do at Oakham School. Sports include cricket, rugby, hockey, athletics, netball and swimming as some of the richest in terms of items in the sub-series.

Most sub-series have a good photographic record of first teams, alongside comprehensive fixture and team lists. Some sub-series will contain correspondence, programmes and administrative documents.

There is an extensive collection of trophies and shields awarded to pupils and Old Oakhamians for their sporting achievements.

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.

Thirteen photographs (A to M) of a dinner in Old Hall. Some of the attendees include Tony Little, Headmaster and teachers. Date is unknown.

A group of photographs (A to P) of Tony Little's leaving do in Stumps in 2002.

This sub-file focusses on minutes of Parent/Teacher Committee meetings during the headmastership of Richard Bull (1978-1984).

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

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 relates to Hodge Wing, the pupils and staff and the history of the building. The series focuses on the early years as a boys' house.
Hodge Wing was a Boys’ day house, for Lower and Middle School. It became a girls’ house in the Winter term 1975, until the Spring term 1980 when the girls moved to Rushebrookes. Then it was re-opened for a small number of Seventh form girls in 1986.

A booklet aimed at Lower School tutors, detailing the tutorial programme of the year, containing various essential points to cover in First and Second forms, guidance on bullying, healthy eating, road safety, stranger danger, sex, smoking, alcohol, drugs, and listing reference videos and books.

This file focusses on Rugby fixture and results.