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This sub-series focuses on photographs of boys, living in Junior House/Chapmans since its inception. The bulk of the collection gathers photographs from the 1950s to 1980s.

This series focusses on the headmastership of John David Buchanan (1958-1977) and contains items relating to the life at School in the 1960s and 1970s, its staff and pupils. The bulk of the series consists of books, publications, letters, speeches and sermons written by Mr Buchanan himself.

An edition of Matkin's almanack including a section on Oakham School on page 16.

A group of original photographs and print-outs used as illustrations in John Barber's "The Story of Oakham School".

A photograph of Oakham School staff in the late 1950s/early 1960s, under Headmaster John Buchanan.

This collection covers the multitude of sports that pupils can do at Oakham School. Sports include cricket, rugby, hockey, athletics, netball and swimming as some of the richest in terms of items in the sub-series.

Most sub-series have a good photographic record of first teams, alongside comprehensive fixture and team lists. Some sub-series will contain correspondence, programmes and administrative documents.

There is an extensive collection of trophies and shields awarded to pupils and Old Oakhamians for their sporting achievements.

A photograph of the 'Big Four' at Minehead in spring 1984.

A negative of the 'Big Four' standing outside the War memorial Library in 1966.

A photograph of the 'Big Four' standing outside the War Memorial Library in 1966. The photograph was taken by Photo-Reportage Ltd and the number is print is stamped on the back: 862848.

A photograph of Junior House boys eating in the house Dining Room, possibly in the late 1950s/early 1960s. This photograph was taken by Photo-Reportage Ltd and the print number is stamped at the back: 157523. The number 23 is written on the front, in the bottom right corner.