A photograph of the 21 Club in 1959. Names are written on the back.

A photograph of the 21 Club in 1961. Names are written on the protective paper cover.

A photograph of the 21 Club in 1966.

A certificate from the Diana Princess of Wales Memorial Award for Young People in recognition of students who have made a real difference to tackling bullying in their school communities awarded to Jerwoods Film Activity in the academic year 2005-2006.

A book recording events and trips of the Oakham School Exploration Society since its inception in Spring term 1978. A badge of the society is glued on the cover.

A letter from Upper School pupil Sujata Rana to Parents and Guardians encouraging membership in Oakham School Politics Association in 1984.

P.N. Davis's subscription card to the 21 Club.

A collection which charts the various societies and activities available to pupils at Oakham School. Documents include photographic records and correspondence for different societies. Topics include chess, CCF/OTC, scouts, Duke of Edinburgh Award, Oligoi , Exploratory Society, and trips and expeditions.

The multiple series contain administrative documents for the various societies and certain series, such as Duke of Edinburgh Award and CCF/OTC have excellent photographic record of formal or informal events.

There is a particularly detailed series on Chess and the event of Gary Kasparov's visit to the school.

There is a good collection of shooting medals and trophies, kindly donated by Henry Blagg.

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.