In October 1939, early in the Second World War, the school had its first experience of hostilities when a German Junkers Ju 88 flew low over the school playing fields en route to bomb Rosyth Dockyard. Kimmerghame House was requisitioned for use as a section of the mine research unit HMS "Vernon". A total of 118 former boys died in the Second World War. In the mid-1940s Sean Connery, a milkman with the St. Cuthbert's Co-operative Society, delivered milk to the school in the mornings.