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This collection covers the multitude of sports that pupils can do at Oakham School. Sports include cricket, rugby, hockey, athletics, netball and swimming as some of the richest in terms of items in the sub-series.

Most sub-series have a good photographic record of first teams, alongside comprehensive fixture and team lists. Some sub-series will contain correspondence, programmes and administrative documents.

There is an extensive collection of trophies and shields awarded to pupils and Old Oakhamians for their sporting achievements.

The items are two copies of E. Pickering-Clarke's register of Oakham School, with different hand-written notes and amendments.

A copy of the "Register of Oakham School, 1900-1950" compiled by E. Pickering-Clarke, owned by Rev Terence Treanor. With hand-written notes on the roll of honour. Enclosing a letter to General Pollard regarding OOs who served in the Royal Leicestershire Regiment and a photocopy of the Roll of honour.

A copy of the "Register of Oakham School, 1900-1950" compiled by E. Pickering-Clarke, owned by Rev Terence Treanor. With hand-written notes on the roll of honour.

A bound copy of several Oakhamian Magazines from 1920 to 1928.

Old Oakhamian Calendar, published in 1927. Cover with contents: Frontispiece; Editorial; Names and Addresses of Members of the Old Oakhamian Club; Annual Dinners; Presentation to Mr J.C. Clark; The Headmaster's Letter; Cambridge Letter; Review of School Games, 1924-1927; Mr J.C. Clark's Trip to Canada; Births, Deaths and Marriages; Old Oakhamian Notes; Cricket and Football Matches; School Staff - September 1927. Thirteen double-pages A to M.

This sub-series focuses on the Dedication of the War Memorial Chapel on 29 October 1925.

An Oakhamian Magazine supplement. Includes photographs of the new Chapel, the order of service for the dedication on 29 October 1925, a report on the ceremony and a brief history of the building. The item belonged to E. Puckering-Clark. Six double pages A to F.

A bound copy of several Oakhamian Magazines from 1926 to 1931.

Old Oakhamian Calendar, published in 1930. Cover with contents: Frontispiece; Editorial; Names and Addresses of Members; Annual Dinners; Headmaster's Letter; Mr J. Story's Letter; Quinquennial Luncheon and Meeting; Resignation of Mr W.L. Sargant - An Appreciation; The Captain of the Ship; Presentation to Mr W.L. Sargant; Cambridge Letter; The Book of Oakham School and The Register; Births, Marriages and Deaths; Cricket, Football and Shooting Matches; The Golfing Society; Club Notices; School Staff. Eighteen double-pages A to R.