Jack had spotted Dicky playing for local team Marsden Welfare Juniors.
Dicky played in the Colts for Middlesbrough and guested for Dunfermline Athletic, whilst working as a Bevin Boy in Scotland at the end of World War II.
His debut for Middlesbrough was in the 1–0 away win against Newcastle United on 7 October 1944 as a 17-year-old in wartime competition, and he played in Boro's first post-war game against Manchester City aged 18.
During his time at Middlesbrough, Dicky went on two FA tours with the England team to Switzerland, Portugal and Scandinavia, yet never gained a full cap.
Dicky also went on to gain the following English League representative honours: During his time at Middlesbrough, Dicky also won the Players 'Footballers Association' Golf Championship at Childwall, Southport in 1951, with his manager David Jack acting as his caddy.