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This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

A collection which charts the various societies and activities available to pupils at Oakham School. Documents include photographic records and correspondence for different societies. Topics include chess, CCF/OTC, scouts, Duke of Edinburgh Award, Oligoi , Exploratory Society, and trips and expeditions.

The multiple series contain administrative documents for the various societies and certain series, such as Duke of Edinburgh Award and CCF/OTC have excellent photographic record of formal or informal events.

There is a particularly detailed series on Chess and the event of Gary Kasparov's visit to the school.

There is a good collection of shooting medals and trophies, kindly donated by Henry Blagg.

Order of service of a service of Commemoration marking the death of Her late Majesty Queen Elizabeth II held in Chapel on 9 September 2022.

This sub-series related to memorial services held in the School Chapel in memory of pupils, Old Oakhamians and staff members who passed away.

A letter and form from Headmaster G. Talbot Griffith to Mr Taylor regarding Coronation Exeat in 1953.

A letter from the Headmaster Tony Little to Nigel Richardson, Headmaster of the Perse School, regarding the Golden Jubilee and sending photographs of the Queen's visit in 1984.

A newssheet from the Headmaster Richard Bull listing the achievements and events of the Winter term 1984.

This file focusses on newsletters, reviewing the terms' events and achievements.

A letter from the Headmaster Richard Bull to Parents regarding the fees for music lessons, the scholarships, the Royal visit, and future term dates.

This series focusses on the headmastership of Oliver Richard Sylvester Bull (1977-1984) and contains items relating to the life at School in the 1970s and 1980s, its staff and pupils. One of the files relates to Michael Stevens as Acting Headmaster for two terms in 1985.