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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 photograph of the guests, staff and former staff, attending the celebration of the 50 years of Deanscroft/Haywoods in 1998.

A photograph of the Headmaster Tony Little giving a speech on his last School Assembly on Doncaster Close in 2002.

A group of negatives (A), index (B) and photographs (C to AK) of the 30 years of Co-Education celebration outside the Library, gathering former headmasters and their wives, and the first girls' cohort.

A photograph of the Headmaster Tony Little, his wife Jenny and their two dogs. Date is unknown.

A photograph of the Headmaster Tony Little and members of the 2001 Decem, including the Head Boy and Head Girl, Guy Hurwood and Kate Campbell, and Katie White and James Bowerman.

A photograph of the Headmaster Tony Little attending an event in the Library, possibly an Old Oakhamian event, with Michael and Mary Stevens. Date is unknown.

A photograph of the Headmaster Tony Little at an event with pupils. Date is unknown.

A letter from the Headmaster Tony Little to Parents regarding a review of the Summer events, before the start of Winter term 1999. Contents: Timings of the first day of term; Expeditions; Maintenance work; Public Examination Results.

Three letters between Eileen Buxton and the Headmaster Tony Little regarding the death of Robert Henry Buxton, and the donation of his Oakham School crest to the School in 2001.