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A collection of documents relating to the Wilson Fields and cricket pavilion, including photographs of the opening. In 2005, the Springfield Playing Fields on Ashwell Road were renamed the Wilson Fields, to honour O.O. Lynn Wilson ('57). Lynn Wilson also funded the construction of a pavilion on the fields. The official opening ceremony took place on 16 May 2005.

A collection of documents, chiefly photographs, of Wharflands, purchased by the then Headmaster Walter Lee Sargant in 1920. The property was converted into a boys’ boarding house for twenty-six boys, while the Old Stables were used for other school purposes. Extension work began in 1928, adding four new dormitories and a large dining hall. The O.T.C. established its headquarters in the new extension. With the boys now living in the extension, the Housemaster and his family could occupied the old house. The first floor was converted into some classrooms, for the teaching of Science and Maths. In 1960 and 1977, a series of improvement and refurbishment work started and changing rooms were modernised, while new rooms were added.

The items in this sub-series are guidelines and resources related to mental health and wellbeing. Most are documents sent internally and externally to staff, parents and guardians.

This sub-series focuses on start and end of term services held in the School Chapel.

This sub-series relates to weddings celebrated in the School Chapel over the years.

Photographs of the War Memorials built on school campus in memory of Old Oakhamians who fell in the First World War, the Second World War and other conflicts.

Various editions of "The Book of Oakham School", written by Walter Lee Sargant.

This sub-series is related to Oakham School's Voluntary Action and includes invitation, programmes, photographs and publicity on events organised by the pupils as their Service.

The items in this collection are related to Tutoring at Oakham School, either guidelines to staff or resources to use in tutorial with the pupils.

This sub-series focusses on tournaments held at Oakham School, in particular reports on games and results.