This series relates to the history of Oakham School Army, Naval and Air Force contingents since 1910, and of the Boy Scouts. Most of the collection is made of photographs from the mid-20th century.

This sub-series relates to the history of the Cadets at Oakham School since 1910. The bulk of the collection is made of photographs of inspection throughout the 20th century.

This sub-file consists of a letter from Robert Gregory enclosing photographs of the Centenary Inspection of the C.C.F. by The Duke of Gloucester in May 2010.

This sub-file contains a photograph of Amanda Clements, sent by Lt Col R.C. Gregory to Dr Joe Spence, Headmaster.

A collection which charts the various societies and activities available to pupils at Oakham School. Documents include photographic records and correspondence for different societies. Topics include chess, CCF/OTC, scouts, Duke of Edinburgh Award, Oligoi , Exploratory Society, and trips and expeditions.

The multiple series contain administrative documents for the various societies and certain series, such as Duke of Edinburgh Award and CCF/OTC have excellent photographic record of formal or informal events.

There is a particularly detailed series on Chess and the event of Gary Kasparov's visit to the school.

There is a good collection of shooting medals and trophies, kindly donated by Henry Blagg.

A note from Lt Col R.C. Gregory to the Headmaster Dr Joe Spence regarding a photograph of Amanda Clements on a C.C.F. Orienteering course and the upcoming C.C.F. Centenary.

A letter from Robert Gregory to Martin Minshall congratulating him on a wonderful occasion and enjoyable lunch at the C.C.F. Biennial Inspection on 5 May 2006.

A letter from Robert Gregory to the Headmaster Dr Joe Spence thanking him for an enjoyable day at the C.C.F. Biennial Inspection and Reunion on 5 May 2006.

A letter from Robert Gregory to the Headmaster Graham Smallbone regarding the acquisition of the stop butt of Brooke Road Rifle range in 1906.

A letter from Robert Gregory enclosing photographs of the C.C.F. Inspection by The Duke of Gloucester in May 2010.