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

A letter from the Headmaster Graham Smallbone to Bryan Waites at the Rutland County Museum regarding celebrating the 450th anniversary of the birth of Archdeacon Robert Johnson and an article in This England.

A letter from Roger Blackmore to Alan Grieve regarding future OSEL events.

This collection covers the history of all the libraries of Oakham School as well as the creation and daily working of the archives.

The Library series has material relating to each regeneration of the library (Smallbone, War Memorial). There is a rich photographic record of the opening and daily running of the Smallbone Library accompanied by administrative documents such as catalogues.

Under the Archives series, material cover correspondence with external readers and research into the history of the school and its pupils. There are also archive committee meeting minutes which show the evolution of the archives from its inception in 2010.

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.

The Oakhamian Magazine and The Old Oakhamian Magazine, recording the Winter term 2014 and Spring term 2015. Contents: News; Features; Academic; Trips and Tours; Performing Arts; Pastoral; Community Activities; Staff News; Sport; Beyond Oakham; Old Oakhamian; Foundation.

A photograph of three generations of Wharflands Housemasters an their wives: Val Harvey, John Barber and Malcolm Hardy.

A bound copy of several Oakhamian Magazines from Spring 1984 to Summer 1987.

The Oakhamian Magazine, recording the Quatercentenary events throughout the year 1984. Contents: 1984 - A Personal View; A Backward Glance; Main Events; Summer Term Festivities; The Royal Visit; Other Opening Ceremonies.

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.