Roles was born in Southampton and attended the Deanery School, becoming an apprentice engineer. He represented Southampton and Hampshire Schools and played his youth football with Albion Boys Club. While playing in the Southampton Junior League, he was spotted by scouts from
Southampton and joined them as an amateur in 1938. By the time he turned professional in October 1940, League football had been suspended because of the war, but Roles made 188 wartime appearances, more than any other Saints player. Roles was not
conscripted during the war because his employment, making engines for torpedo boats at
Parsons on the Town Quay, was a
reserved occupation. During the war, Roles also made at least one guest appearance for
West Ham United. Described as a "mobile left-back", In the summer of 1946, Roles was called up to do his
National Service and before he returned to
The Dell in 1948, his position at left back was occupied by
Bill Rochford who had been signed in July 1946. On his return to the club after his National Service, Roles was placed on the
transfer list, but was re-engaged for the start of
the 1948–49 season. Roles had to wait until 4 April 1949 before he was selected again for the first team, when Rochford was unavailable for the trip to
Bradford Park Avenue. At this time, Southampton were eight points clear at the top of the
Second Division table with seven matches left to play and were confident of promotion. In the event, Southampton (also without top-scorer,
Charlie Wayman) lost 2–0 at Bradford and only won once in the final six matches, missing promotion by one point. In May 1949, Roles was released by the club, and joined
Gloucester City for a brief spell before becoming player-manager at
Cowes. ==Later career==