This series focusses on the headmastership of Walter Lee Sargant (1902-1929) and contains items relating to the life at School in the early 20th century, its staff and pupils.

Magazine named "The Old Oakhamian", on paper; 4 pages; contents: Annual Dinner, Old Oakhamian Fund, Cricket, Football and Golf, School Notes, Births, Marriages and Deaths, In Memoriam, Old Oakhamian Notes, Notices

A5 magazine named The Oakhamian, stappled; 24 pages; contents on the inside cover: War Memorial, School News, Speech Day, Cricket, Swimming Sports, Music Notes, O.P.R.S., Into Thin Air, Chess Club, Debating Society, J.T.C., Scout Notes, Rugby Football, Junior House Plays, Correspondence, O.O. News

A5 magazine named The Oakhamian, stappled; 20 pages; contents on the inside cover: Roll of Honour, School News, Frank Emerson Chapman, Music Notes, J.T.C., A.T.C., Scout Notes, Swimming Sports, Football, Correspondence, O.O. Notes

A5 magazine named The Oakhamian, stappled; 31 pages; contents on the inside cover: Roll of Honour, Editorial, School News, J.T.C., Scout Notes, Music Notes, J.C. Clark, Junior House Play, Boxing, the Sports, Junior Sports, Oakham School 50 years ago, Virgiliana, The Creation, As Others See Us, Cricket, O.O. News, O.O. Golfing Society, Football Fixtures, Correspondence; hand-written "DJ Stocks Junior House Oakham Rutland"

This series focusses on the headmastership of Grosvenor Talbot Griffith (1935-1958) and contains items relating to the life at School in the mid-20th century, its staff and pupils.

A letter from Charles Sills and photographs of C.C. Sills and Junior House

This file focusses on roll call lists from the early 20th century, under the headmastership of Walter Lee Sargant.

This file focusses on roll call lists from the early 20th century, under the headmastership of F.C. Doherty.

A roll call for the Summer Term, presented by Maxwell Heron from John Heron's collection.