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This series focusses on the headmastership of Tony Little (1996-2002) and contains items relating to the life at School in the 1990s and early 2000s, its staff and pupils.

Bound Copy of several Old Oakhamian Issues; red and black, hard cover

Magazine named The Oakhamian, stappled; glossy cover with a photograph of Garry Kasparov and two pupils; 31 pages; contents: VIP Visitor, Gap Year, English, History, Community Service, Performing Arts, Art, Sports, Miscellany, Languages, Houses; with various photographs of staff, pupils, plays, sports, trips

An album/ scrapbook recording the history of the Schanschieff site, Rutland independence, photos of the house (external and internal) as well as of Clipsham and Barrow. Conains mood boards for colour schemes and designs of each of the houses. Also contains fabric samples. Has photos of the Simon Schanschieff portrait at the back with the artist Jume Mendoza; also Graham Smallbone and Pippa Schanschieff

A collection of documents, mostly photographs, relating to the Schanschieffs site.
In 1994, the School purchased the Catmose Vale site, behind Rushebrookes house. The original buildings were built in 1836-1837 by William J. Donthorn. They used to be the town’s workhouse, which later became the Catmose Vale Hospital. On the site was built a car park, two Day boys’ houses and the original buildings were converted into two Day girls’ houses. The four houses were officially opened on 17 September 1997 and were named after Rutland villages: Gunthorpe and Hambleton (Day girls), and Barrow and Clipsham (Day boys). The site was named after O.O. Simon Schanschieff ('57), Chairman of the Trustees.

A4 magazine, stapled; 12 pages; "2 Chairmen, 5 Headmasters and 4 new houses" headlines with various photographs of headmasters, girls and boys walking on campus on the cover; contents: All your Yesterdays, Oakham 1940-45, O.O. News, , Gardens & Grounds, Obituaries, Cricket World Trophy 1997

Bound copy of several Oakhamian Magazine; hard, black and red cover

This series is related to the buildings on the School campus and documents their history. Most of the collection is made of photographs and artwork, as well as architectural plans. Each sub-series focusses on a different building.