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A letter from the Headmaster Graham Smallbone to Idris Evans at Oakham Town Council regarding the Official Street Plan in 1986.

A letter from the Headmaster Graham Smallbone to Parents regarding a review of the Spring term 1996. Contents: Drugs guideline; Events of the term; the Hospital Site.

A letter from the Headmaster Tony Little to Parents regarding a review of the Winter term 1996. Contents: Achievements in Drama, Music and Sports; Parent/Teacher Committee; Matters Academic; Building Development; Staff.

A memorandum from T.M. Reay, Bursar, to John Lake, Appeal Director, regarding the Barber Archive Room in the new Information and Study Centre.

Four pages (A to D) from a 1919 photo album, with captions below the photographs. Contents: Main entrance (School House), pupils after school fire, 1919; 'Tudor House' in Boughton; Rugby 1st XV, 1919; Burleigh gardens and pond; Old Hall and the quad; A cricket match; Lord French inspecting the cadets; St John's College; pupils in the quad; the Long Dormitory boys; a dog; Coates, 1919; pupils at the baths; Burleigh woods and hill; Market Place; F.C. Dwyer; Cricket 1st XI, 1919; The Rectory; C.F. Bayley.

This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

Printed Powerpoint slides from a presentation on the centenary of Chapmans. Includes information on the school's founding, images of various school buildings from different times, campus maps and pupils; a history of Junior House/Chapmans House; and a list of Housemasters. Thirty-four pages A to AG.

A list of improvements to the School premises in the 1930s, compiled by Headmaster G. Talbot Griffith for Old Oakhamians. Enclosed are photographs of buildings. Five pages A to E.

A photograph showing Upper School boys leaving the Deanscroft Studies, probably in the 1960s.

A photograph of Upper School boys standing outside the Deanscroft Beach Studies, probably in the 1960s.