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This sub-series is related to the organisation of the Rutland Water Walk for charity. Items include correspondence, map and route details, safety rules and guidance for pupils and staff.

A list of all school staff and their role during the Rutland Water Walk, either walking, manning checkpoints or driving a minibus. Five pages A to E.

A booklet containing the programme for the Charity Walk, staff duties, the route, checkpoints and transportation arrangements. Six pages A to F.

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 series contains various account books, cash books fees books and ledgers recording pupils fees and other charges, incomes and expenditures, staff wages and salaries throughout several years.

Individual salary and wages sheets for teaching and support staff between 1937 to 1960. Pages A to BB.

A salaries cash book, recording salary, payments, tax, and lunch for teaching staff, admin staff and matrons, from May 1963 to November 1965.

The items in this collection are related to Tutoring at Oakham School, either guidelines to staff or resources to use in tutorial with the pupils.

Guidelines on the Tutorial system at Oakham School, presented to a staff seminar on 24 June 1986 by the Headmaster, Graham Smallbone. The paper discusses safeguarding and pastoral issues that might be encountered and mentions what is expected of a tutor and how they should behave. The four pages are numbered A to D.

Guidelines for Middle School Tutors, detailing their general responsibilities and their pastoral role at Oakham School. Two pages numbered A and B.