This sub-series focusses on press cuttings, magazines and other publications reporting on chess tournaments at Oakham School, on Oakham School Chess team competing in National Championships, and the development of chess at Oakham School.

A newspaper article reporting on Oakham School winning against Southend School to reach the quarter finals of the 2002 National School's Chess championship.

A letter from Anne Rawlins to Parents informing them of two training sessions at Oakham RFC for their children before the Leicestershire Cross Country Championship at Braunstone Park in 1999.