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A collection of photographs of the QET since the transformation of the Barraclough Hall as part of the Quatercentenary Development Plan. The architect, W.O. Wilson, had designed a modern auditorium, with raked seating and a large stage below the audience, a gallery and a foyer facing the Music School lawn and purpose-built rooms for changing, costumes, scenery making and storage. It was equipped with a computerized lighting system and sophisticated sound equipment. The new Oakham Theatre was officially opened on 16 November 1984 by Queen Elizabeth II.

A letter from David Tew thanking John Barber for sending a copy of his book "The Story of Oakham School".

A photograph of the High Sheriff of Rutland, Major Herbert Whaley inspecting the C.C.F. cadets at the proclamation of Queen Elizabeth II in Market Place in 1952.

A letter from Alwyne Westmoreland to the Headmaster, John Buchanan, apologizing for not being able to participate in the next Development Campaign. Two pages A and B.

An A1 poster with photographs of five house events in the Spring term 2020: a Fifth Form tutor outing to Wildwood in town after their mock exams; a Third form social with Buchanans; Rushebrookes Senior Netball team competing in the 2020 Interhouse Netball; Quiz night organised by the prefects; Rushebrookes girls on a paintballing trip at the weekend.

A wooden shield awarded by Rotary Club of Rutland at the Rutland Debating Festival in memory of P.P. 'Pop' Westmoreland. The shield has one central medallion and nineteen small metal medallions, nine of which are engraved with the wining school and year. Oakham School won in 1987, in 1992 and in 1995. Other winners are Uppingham Community College, Uppingham School, Vale of Catmose College and Casterton Community College.

A blank post card showing the interior of the Chapel, made by Heawood & Son, Melton Mowbray and Oakham.

A blank post card showing a procession leaving All Saints' Church on Speech Day in 1924, published by Heawood & Son, Melton Mowbray and Oakham.

A blank post card showing the Dr Theodore Woods, Bishop of Winchester, laying the foundation stone on Speech Day, in 1924. The post card was published by Heawood & Son, Melton Mowbray and Oakham.