Prior to the First World War Sherriff attended Kingston Grammar School. Surviving educational certificates confirm that he passed his school examinations, but he does not seem to have won any academic prizes. A school report from 1908 states that he was a “satisfactory” if not outstanding student, ranking fifth overall in a form of 20 boys for academic achievement.
Sherriff shone on the sports field rather than in the classroom. Scrapbooks of newspaper cuttings reveal that he won various sports prizes at the school over the years. As well as taking part in cricket matches and rowing races, he also played hockey and was a fine athlete.
During his time at the school he made friends with boys whom he remained close to until the war, during which several of them were tragically killed in action. One of the friends who survived the war was Cyril Aubrey Manning-Press, who later became a banker. Correspondence between Sherriff and Cyril survives which dates from the First World War until the 1940s, revealing a shared enthusiasm for the theatre and amateur dramatics.
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