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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.

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.

A photograph of boys on their bed in one of the dorms in Deanscroft, probably in the late 1970s.

A photograph showing boys walking on the path, leaving Deanscroft, probably in the 1960s.

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.

The Standing orders of Deanscroft in 1958, including the daily routine of the house and rules. The item was owned by T.C.F. Blagg and presented by Henry Blagg. Four pages A to D.

A book recording the house officials for Deanscroft, as well as the boys who were on house duties (or 'fagging'), from Christmas term 1947 to Winter term 1988.

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 photograph of boys on their bed in one of the dorms in Deanscroft, probably in the late 1970s.