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This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

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.