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This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

A sermon given by Headmaster John Buchannan at Speech Day 1959, relating to St Paul's address to the Corinthians and the sporting metaphor of the Christian life. The sermon is typed, with hand-written notations. Nine pages A to I.

A letter from the Headmaster Richard Bull to Michael Stevens, Patrick Wilson and Housemasters regarding recommendations for the Anderson Awards.

This collection highlights the depth and breadth of the school's curriculum and pupil's work. The drama and music sub-series are particularly detailed with their collection of production stills and programmes.

CUR/7 contains reports relating to the school's teaching and curriculum alongside timetables for lessons and exams, and comprehensive examination results for GCSE, A Level and IB.

Throughout the series in this collection, there is material relating to events and trips undertaken by various departments to increase the extra-curricular activities of pupils.

Oakham School Magazine, recording the Summer term 1897 (published in Winter term 1897). Contents: Editorial; School Notes; Old Oakhamian Club; In Memoriam; Prize Day; Cricket; Correspondence. Nine double-pages A to I.

Oakham School Magazine, recording the Summer term 1901 (published in Winter term 1901). Contents: Editorial; School Notes; Speech Day; Football; Cricket. Seven double-pages A to G.

Oakham School Magazine, recording the Summer term 1904 (published in Winter term 1904). Contents: Editorial; School Notes; Prize-Giving; Swimming Sports; Cricket.

Oakham School Magazine, recording the Summer term 1905 (published in Winter term 1905). Contents: Editorial; School Notes; Shooting Match; Swimming Sports; Death of Dr Ellicott; Speech Day; The Cricket Season. Seven double-pages A to G.

Oakham School Magazine, recording the Summer term 1911 (published in Winter term 1911). Contents: School Notes; Speech Day; The Officers' Training Corps; Swimming Sports; Cricket. Seven double-pages A to G.

Oakham School Magazine, recording the Summer term 1913 (published in Winter term 1913). Contents: School Notes; Swimming Sports; The Officers' Training Corps; Speech Day; Cricket; Football Prospects for 1913. Seven double-pages A to G.