Born in Seaton Delaval, Stephenson originally played for Aston Villa in 1910 as an inside forward; his career at Villa Park totalling 216 matches, from which he scored a reasonable 85 goals. He was brought into Villa Park as Villa legend Harry Hampton's career was nearing its end and soon acquired a reputation for intuitive play: his passes were said to be "as sweet as stolen kisses". His first silverware came in the 1913 FA Cup Final alongside Hampton and England national team player Joe Bache in the victory over League Champions Sunderland; the only occasion in English football history when the FA Cup Final was contested between the top two clubs in The Football League. Stephenson claimed before the 1913 FA Cup final to have dreamt, that Villa, would beat Sunderland with a headed goal from Tommy Barber. Villa did indeed win that final with a headed goal from Tommy Barber. Stephenson was to play in the semi-final the following year and was a winner in the FA Cup final in 1920 in what proved a fitting swansong for the club.