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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 Day boys' house Barrow, founded in 1997. The main items are house photographs and handbooks.

This series focuses on the Junior House/Chapmans pupils and staff since its opening in 1910. It first comprised the Junior Department with facilities for boys boarders and classrooms. The house was renamed Chapmans in September 1960, after Frank Emerson Chapman, first Housemaster of the Junior House; it became a Senior House. Most of the series is made of photographs, house photographs as well as more informal photographs.

This series focuses on the Day boys' house of Johnsons, throughout its history (1959-1997). The collection is mostly made of house photographs and teams' photographs, as well as some administrative records.

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

This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

This series focuses on Round House pupils and staff since its opening in 1972 as the first purpose-built girls' boarding house. Most of the series is made of photographs, house photographs as well as more informal photographs focussing on house events.

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.

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 is made of various items which did not fit in any other series in the CHA collection.