This sub-series focusses on informal photographs of the Haywoods' boys in house.

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.

A photograph of five girls outside Rushebrookes house, going on a 5km Charity house in 2018. The walk took place throughout the longest night of the year but this photograph shows the girls who were unable to do it on the set date and did it at a later day with the Housemistress, Tessa Drummond.

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 sub-series focuses on the history of the Junior School, renamed Chapmans in 1961.

This sub-series focuses on the daily and running of Deanscroft. It includes house rules and house duty lists.

A photograph of Emma Bebb at the start of 1991 Winter term in Stevens House.

A photograph of Sue Lewis at the start of 1991 Winter term in Stevens House.

A photograph of Anna McErlain at the start of 1991 Winter term in Stevens House.

A photograph of Anstey Brock at the start of 1991 Winter term in Stevens House.