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This series is made of marking books. The bulk of the series consists of books donated by Jan West.

This series focusses on Oakham School policies. The bulk of the series relates to the Staff code of conduct.

This series focuses on the boarding girls in Rushebrookes house. It was named after the first School Headmaster, Robert Rushbrooke. The first girls moved in in the Spring term 1980 but the building was officially open only on 22 November 1980. This series contains items related to the daily life of the girls in school and in house, as well as house photographs, mostly from the 2010s.

This series focuses on the boarding girls in Orchard Close (built in 1929), later Buchanans House. It became a girls' boarding house in early October 1975 and Michael Stevens was its first Housemaster. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982 and the extension was ready for occupation in January 1983. The house was first a Seventh Form house and transitioned to a Middle School house in the 1980s.

This series focuses on the pupils and staff of Haywoods, a boys' boarding house opened in 1989. This series is uncomplete. We are missing all the house photographs and are hoping to build up this collection.

This series relates to College House, the pupils who lived there and the history of the building.
College House was built c.1320 and used to be a priest’s house for clergy sent to the town by Westminster Abbey. Oakham School bought College House from the Church in 1736. It served as the school’s Sanatorium until 1965, when College House was then converted into a boarding house for a dozen potential Oxbridge candidates.
In 1971, College House became the first girls’ boarding house. In 1982, it was converted to be used as a Seventh Form Study Centre.
Since 2007 College House has been converted into offices. The Foundation and Marketing moved in and the Senior Deputy Heads use the wing as their private residence. The Barber Rooms, housing the School Archives, opened in 2010 on the first floor and the Old Oakhamian Club is now on the ground floor.

This series focuses on the Day boys of Clipsham, founded in 1997. The main items are house photographs and handbooks.

This series focuses on Peterborough House pupils and staff since its inception in 1966. Most of the series is made of house photographs, house magazines from the 1970s and various administrative documents.