Sydney was born in 1916 in Rhodesia, Eastern Cape, South Africa to Phillip who worked as a furrier and Tobie Schragger and he had two brothers Herbert and Louis.

Records state that Sydney enlisted in the Middle East and trained as a pilot. Sydney was the pilot of Blenheim V6504 which departed from Dohazari airfield on an air test. The aircraft lost a propeller and dived into the ground from 1000 feet south of Yelahanka killing both Sydney and his observer William Edward Brister, 1152420.