This sub-series focuses on various events organised by the girls of Gunthorpe house, in particular Charity events.

A certificate commemorating Oakham School's success of 5,000 Duke of Edinburgh Awards.

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

Stretching back to the headmastership of Dr. Doncaster, this collection comprehensively covers the correspondence, publications, photographs and other ephemera of the headmasters of Oakham School up to the present day. For many of the headmasters, correspondence and rolls calls are a significant theme in their series.

This collection also contains an excellent record of speeches and sermons given by G. Talbot Griffiths and John Buchanan.

The final series on reports covers the headmaster's, deputy headmaster's and registers writings on the state of the school, including topics such as building and estate development, admissions, the curriculum, examination results, and Old Oakhamians.

This series focusses on the headmastership of Henry Price (2019-today) and contains items relating to the life at School in the 2020s, its staff and pupils.

A poster advertising an Oakham School Medical Society event with Old Oakhamians discussing Medicine careers held in the Wilson Auditorium on 23 March 2022.

A poster advertising an online meeting with Old Oakhamians discussing Science careers. The meeting took place online over lockdown in Summer term 2020.

A poster advertising a special meeting of Oakham School Biology Society and a lecture by Sir Venki Ramakrishnan, Nobel Prize in Chemistry. Attached are questions following the lecture. Three pages A to C.

The itinerary of the boarding and day houses' trip to Alton Towers on 16 May 1999, sent by Jan West to houses to be announced and displayed.

A report from Rev John Darrall on the history of the Oakham School Charities Association and listing all the events organised by the school, houses and individuals to raise money in aid of various causes.