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This collection highlights the work and life of Oakham School pupils both during and after their time at the school. The collection has an excellent representation of the careers, work, and exam aspect of school life, including examination results, leaver destinations, work experience and information on Project 20/20.

There are detailed records on the council, Decem and prefects, particularly in their recruitment, meeting minutes, and handbooks.

In several of the series, there is a strong photographic collection illuminating the rich daily life of the school and its pupils. This is shared alongside copies of pupil magazines, arts calendars, and records of pupil achievements.

A list of pupils taking part in the Rutland Water Walk for charity, with names and houses. Ten pages A to J.

A list of pupils taking part in the Rutland Water Walk for charity, with names and houses and a record of their progress to the checkpoints. Ten pages A to J.

Email correspondence between Jan West and Housemasters/Housemistresses regarding pupils taking part in the Rutland Water Walk and attached amended house lists. 32 pages A to AF.

A cash receipts book recording pupils' fees, extras charges and school balance, from Summer term 1939 to the start of Christmas term 1942.

A cash receipts book recording pupils' fees, extras charges and school balance, from Christmas term 1942 to Christmas term 1944.

A fees book recording fees paid by pupils from Easter term 1876 to Christmas term 1879, including personal information such as parents' an guardians' names, addresses, age, entrance and registration fees and lessons chosen.

A cash book recording pupils' fees and other charges on their school bills, from Summer term 1967 to Winter term 1970.

An account book recording pupils' fees from Christmas term 1914 to Christmas term 1924.

This series is related to school fees and tuition. Items include reports from the Bursar on increase of fees, balance sheets, and individual pupils' bills.