He began his career with amateur side Bolton Temperance before signing for First Division club Blackburn Rovers but was released a year later having made no appearances.
Played at Stamford Bridge, the match ended in a 6–2 victory for the English Football League with Shepherd scoring four times.
Signed as a replacement for Bill Appleyard,[6] he made a goalscoring debut for the club during a 4–0 victory over Nottingham Forest but played in a 9–1 defeat to local rivals Sunderland in the following match, scoring Newcastle's only goal via a penalty.
[1][7][8] Newcastle reached the final again the following year, with Shepherd scoring eight times during the previous rounds and winning a second cap for England in a 2–1 victory over Ireland on 11 February 1911.
[8] Contesting a loose ball with Rovers goalkeeper Jimmy Ashcroft, when the pair made contact that resulted in Shepherd damaging ligaments and tearing muscles in his knee.
He scored ten league goals in twenty-two appearances before he retired from professional football following the outbreak of World War I.
He was buried four days later at Christ Church, Walmsley with former Bolton players Joe Smith, Bert Baverstock, Ted Vizard, Billy Jennings, George Eccles and Jimmy Seddon as pallbearers.