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This series focuses on School House pupils and staff in the 20th century. Most of the series is made of house photographs, various informal photographs as well as records books and punishment books.

A photograph of the boys in School House in the academic year 1946-1947 under the Headmaster G. Talbot Griffith.

A list of the Housemasters of School House from 1951 to 2001.

A collection of documents relating to the School's first cricket pavilion. It was built on the playing fields in the 19th century. It was then enlarged and renovated in 1931, when two changing rooms and a thatched roof were added. It unfortunately burnt in May 1970.

A collection of photographs of the School's first cricket pavilion, until it was destroyed in a fire in 1970.

A photographic album of the school (but mainly of Wharflands house) from the Talbot-Griffiths era. Photographs of various staff members, buildings, House prefects, scouts, sporting photos (steeplechase, water-polo, rugby), House photos (Wharflands), Drama photos (Midsummer's Nights Dream and Macbeth 1953), The 1953 Elizabethan Fair, Form 4A photo (1951 and 1953), The choir, the Memorial Library opening, a christening, the visit to RCAF N.Luffenham Swindells, and the proclamation of Queen Elizabeth II.

A letter from Peter North, Principal of Jesus College, Oxford, to John Barber regarding his book "The Story of Oakham School".

This series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

A complete collection of bound books, gathering Old Oakhamian Magazines copies, from 1899 to 2002. Some books may contain issues of the Magazine that would be otherwise missing in the collection.

A photograph of Headmaster Grosvenor Talbot Griffith in his office. The photograph was taken by Photo-Reportage Ltd and the number of print is stamped on the back: 808074.