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A green minute book recording minutes of working party meetings and general meetings of the Oakham School Foundation from the 2000s.

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.

A programme for the Oakham Fashion Show held in the Sports Hall on 18 March 2006 in aid of the Make-A-Wish Foundation.

This series focuses on the boarding boys in Deanscroft, since its opening in 1948. The Headmaster himself was Housemaster, until 1971. Deanscroft boarding house was closed on Speech Day 1989, prior to its conversion into Stevens, a boarding house for girls. The boarding boys were moved to the newly built Haywoods House on Kilburn Road. The items include the complete set of house photographs and informal photographs showing boys around the house and on campus, as well as duty records.

This sub-series is made of various informal photographs of the boys in Deanscroft, especially in the 1960s. It also contains items related to the 50 years Anniversary celebration of Deanscroft & Haywoods House, including a tie designed for the special occasion.

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

A guest list for the celebration of the 50 years of Deanscroft/Haywoods. Guests include Old Oakhamians and the dates when they attended school, and staff. Two pages A and B.

This sub-series focusses on various photographs of the pupils and staff of School House as well as various documents related to the history of the house.

This sub-file contains various photographs of the girls in their boarding house, as well as various items recording the every day life and events in Buchanans House.

A menu for Buchanans and Haywoods Sixth Form Guest Night held on 22 January 2011 in the Barraclough. With signature of some of the attendees.