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Two photographs (A and B) of the portrait of Walter Lee Sargant, painted by Frank Brooks. The portrait dates from the 1920s, and the photographs maybe date from the 1960s.

Items related to Walter Lee Sargant's book "Oakham through the centuries".

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.

The Old Oakhamian Magazine, Sargant In Memoriam number, published in 1957. Contents: Editorial; This Year's President; Annual General Meeting; Annual Dinner; Regional Meetings; School News; O.O. Notes; Engagements, Births, Marriages & Deaths; Obituaries; New Members; Changes of Address; Review - Shadow of the Eagle; Notices; Correspondence; Golf. Twelve double-pages A to L.

Old Oakhamian Calendar, published in 1921. Cover with contents: Editorial; Members of the Old Oakhamian Club - 1920; Letter from the Headmaster with plan; Old Oakhamian Notes; Old Boys' Matches. Six double-pages A to F.

The Oakhamian Magazine, recording the Spring term 1956 (published in Summer term 1956). Contents: School News; Mr Sargant; Speech Day; Avete; Valete; House Transfers; C.C.F.; Shooting; Scout Notes; Cub Notes; The Twenty-One Club; Excavations; Study-Leave in Nepal; Cricket; Junior Sports; Football Fixtures; O.O. News. Nine double-pages A to I.

The Oakhamian Magazine, recording the Summer term 1936 (published in Winter term 1936). Contents: Long Live the King; Editorial; School Notes; Music Notes; Entertainments; Debating Society; O.T.C.; Scouts; Cricket; Swimming Sports; Football; O.O. News; Scholarships to the United States; Acknowledgements. Seven double-pages A to G.

This collection focuses on the staff who have worked for Oakham School over the years. Material focuses on not only training and teaching, but staff wellbeing, pay and benefits.

There are two series which focus on notable members of staff from the school's history: Jon Wills and Brian Welford. Material for these staff members have been collected by themselves and other members of staff.

Recruitment series includes jobs descriptions for various positions, both teaching and support staff, in the school.

There is a strong collection of policies an guidance for teachers in completing the many administrative and teaching jobs expected.

This sub-series is related to services held in the School Chapel since the laying of the Foundation stone in 1924.

A School list of staff and pupils for the Summer term 1903. Contents: Trustees; Teachers; Forms VI to I; Successes since Midsummer, 1902; Oxford & Cambridge Board, 1903; Royal Drawing Society. Five double-pages A to E.