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This file focusses on photographs of Tony Little, during his Headmastership (1996-2002).

This file contains photographs owned by Rev Terence Treanor on various topics: House photographs, Sports team and school events and dinners.

This series focusses on photographs of teaching and support staff throughout the years. The bulk of the collection is individual photographs of staff from the 1990s.

This file focusses on photographs of various Inspections of the Cadets and contingents, as well as group photographs of full contingents since the early 20th century.

A blue photo album of Oakhamians and visitors: Schanschieff's Opening; Little, Alan Duncan MP, Wiliam Hague MP, Tom Lazur, Poppy Moore, Lord Sebastian Coe, Graham Lee, Martin Johnson, Ben Wheeler, Roger Blackmore, Philip Coates, Sheila Hardy, Jane Matthews, Margaret Cousins, Gary Kasparov, Pert, David Garner, Daniel Hyde, Matthew Pilling, Nicholas Branston, sports teams, pupils, a play

A red photo album containing photos of Michael Holford, Mark Meenan, Crista Cullen, Wayne Clark, George Firmin, Fraser Graham, Tom Wignall, Andrew Hazell, David McKee, Matthew Shouler, Guy Jolleys, Pert, Ruth Catallo, Edward Jarron, John Darrall, Roger Blackmore, the Chapel, the Opening of Stumps and team photos

A photograph of the guests, staff and former staff, attending the celebration of the 50 years of Deanscroft/Haywoods in 1998.

This file focusses on matters of the Parent/Teacher Committee during the headmastership of Tony Little.

This series is related to outreach events organised outside lesson timetable, promoting activities at school, supporting the local community and attending events with/for other schools. This series places Oakham School at the centre of the local community.

This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.