Stephenson was a member of the Wanderers club, making his first appearance on 23 October 1869, aged 16. Described as "a most efficient back", he made 19 appearances for the Wanderers before "retiring" in 1873. He played in Wanderers' first two FA Cup ties in 1872 but was missing for the semi-final and final matches.[3]
In February 1871, Stephenson was selected to represent England, as the solitary "back", in the third pseudo-international match against Scotland. The match ended in a 1–1 draw, with goals from Charles Nepean (Scotland) and R.S.F. Walker.[4][5] Stephenson retained his place, now playing in goal, in the England XI for the next two matches, played on 18 November 1871 and 24 February 1872, which ended in victories for England, by scores of 2–1[6][7] and 1–0 respectively.[8][9]
He was a member of the Football Association (FA) committee from 1871 to 1873.[3] On 20 July 1871, C. W. Alcock, as secretary of the FA, convened a committee meeting at the offices of The Sportsman newspaper and proposed "that it is desirable that a Challenge Cup should be established in connection with the Association for which all clubs belonging to the Association should be invited to compete". The proposition was carried and the inaugural FA Cup tournament kicked off in November 1871.[10]
Stephenson also played for the Barnes Club and appeared for London against Sheffield in 1871 and 1872.[3]