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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 series focusses on the headmastership of Francis Cecil Doherty (1929-1935) and contains items relating to the life at School in the early 20th century, its staff and pupils.

An email from Jan West to teaching staff regarding the arrangements for the Walk and reply from Charles Welch

This focusses on various items relating to F.C. Doherty himself or events under his headmastership.

This sub-file contains various photographs of the girls and tutors of Stevens House since its opening in 1989. Most of the photographs were gathered in photograph albums by the Housemistress.

This sub-series is made of various items, such as informal photographs of the girls in Ancaster, house events, house prefects and miscellaneous objects. The bulk of the sub-series focuses on the 2000s.

A box of ephmera from Buchanan's House.

This sub-series focuses on informal photographs of the girls in Rushebrookes, in particular interhouse competitions.

This file compiles reports and accounts of the Oakham School Charities Association since its inception in 1986 until 1999. The items give details on various charity events organised at school, on the charities and causes supported by the school and sums of money raised.

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.