A collection of material from Anna Bentley's office including some school trophies, specially produced Oakham School dictionaries, entry books for the school, financial accounts, exam results, and correspondence. Most of the material in this collection relates to work completed in the marketing, administrative and foundation departments of the school.

Press cuttings from local and international newspapers reporting on the Oakham School Junior Chess tournament in 1992.

This file focuses on various informal photographs of the day girls of Hambleton competing in interhouse competitions, organising bake sales, on trips and other house events. It is believe these photographs relate to the first few years of Hambleton House.

A group of photographs of various trips to France, such as a skiing trip, the Battlefields trip, a trip to Paris and to Giverny to visit Monet's garden.

Chess match reports of Jean-Paul Mercier from 9 March to 29 March 1992 at Oakham School Junior International. Three pages A to C.

This series focuses on the Day girls' house of Hambleton, founded in 1997. The main items are informal photographs of house events and house diaries, planning and detailing the house routine throughout the years.

This sub-series relates to every day life in Hambleton house, as well as various house events held on evenings and weekends. Most of the sub-series is made of photographs of the first few years of the house, since its opening in 1997.