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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.

Thirteen photographs (A to M) of a dinner in Old Hall. Some of the attendees include Tony Little, Headmaster and teachers. Date is unknown.

This subfonds contains the Archive's complete collection of Red books. These books contain a calendar of events for the upcoming term, lists of pupils and their houses, and lists of staff.

A complete collection of Red Books - School lists and Calendars since 1959. Red books give information regarding pupils, tutor groups, teaching and support staff, school calendar and events, school rules, future trips and dates. Only two Red Books were never published, Summer term 2020 and Spring term 2021 as the UK was in lockdown (COVID-19) and pupils were not at School and had lessons online.

This sub-file contains photographs of the opening ceremony of the new Buchanans extension completed in 1983. Former Headmaster John Buchanan was amongst the guests.

This series focuses on the boarding girls in Orchard Close (built in 1929), later Buchanans House. It became a girls' boarding house in early October 1975 and Michael Stevens was its first Housemaster. It was renamed Buchanans House in Summer 1977, following the retirement of Headmaster J.D. Buchanan. Work was completed on Buchanans house in 1982 and the extension was ready for occupation in January 1983. The house was first a Seventh Form house and transitioned to a Middle School house in the 1980s.

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

A booklet commemorating 30 years of Co-Education at Oakham School. Contents: message from John Buchanan, Up to 1970, the Concept of Co-Education, "There were a gallant lot", "For us, Co-Education is no an issue", "30 Years of Co-Education, highlights.

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.