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A wooden shield awarded by Rotary Club of Rutland at the Rutland Debating Festival in memory of P.P. 'Pop' Westmoreland. The shield has one central medallion and nineteen small metal medallions, nine of which are engraved with the wining school and year. Oakham School won in 1987, in 1992 and in 1995. Other winners are Uppingham Community College, Uppingham School, Vale of Catmose College and Casterton Community College.

A collection of reports and financial statements, and letters, related to the activities of Oakham School Enterprises Ltd (OSEL), spanning from 1978 to 1995.

A balance sheet on Oakham School Enterprises Ltd activities for the year ended 31 August 1995.

A balance sheet of the catering costs for Summer Holidays events in 1995.

A balance sheet forecasting OSEL profits for the year 1993-1994.

A letter (A) from Graham Smallbone, Headmaster, Simon Schanschieff, Chairman of Trustees, and Rev Terence Treanor, Honorary Secretary of the Old Oakhamian Club, to former pupils who were at Oakham during John Barber's years with the School regarding celebrating his eightieth birthday and the Barber Archives. Attached is a reply slip (B).

A letter from John Lake, Appeal Director, to former pupils of John Barber's time as well as current parent, regarding the Barber Archive Room in the new Library.

This sub-file focusses on the stay of the National Youth Chamber Orchestra at Oakham School in August 1993, including details of the arrangements, correspondence, and programmes of their performances at Peterborough Cathedral, The Maltings, Oakham School Chapel, and The Proms at the Royal Albert Hall.

A final Directors' report and financial statement on Oakham School Enterprises Ltd activities from the Chartered Accountants K.P.M.G.; including balances, funds, loss and profits.

A letter from Sir Michael Latham congratulating Roger Blackmore on the two pages Times focus on Oakham School.