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Born in Great Lever, Bolton, Lancashire, England, Shepherd had already scored 90 goals in 123 games for his home town club Bolton Wanderers when Newcastle United paid the then record fee of £800 for his services. (Other sources say £850 and £1000). He made his debut for Newcastle in a 4–0 away win at Nottingham Forest a game in which he scored his first goal for his new club. The following week he made his home debut against fierce rivals Sunderland. At half time the score was 1–1 with Shepherd having scored Newcastle's goal from a penalty but in the second half Sunderland scored 8 more goals without reply and won the game 9–1. This still stands as Newcastle's biggest ever home defeat. Undaunted, both Newcastle and Shepherd went on to have a fine season in which the club won the First Division Championship and Shepherd ended the season as Newcastle's top scorer with 15 league and cup goals. Shepherd was known for having a ferocious shot which on some occasions even carried the goalkeeper over the line as well as the ball. He was also noted for being a very charismatic and playful character. At half time in an away match at Notts County with the score at 0–0 he asked the Newcastle officials if he could leave the field of play early so as to catch a train to Bolton to visit his family. Newcastles' then Chairman Joe Bell, himself a popular and jovial character, told Shepherd that if he scored four goals he could leave as soon as he liked. Shepherd duly scored four goals in the second half and according to the sports writer Arthur Appleton, "developed a sudden limp" and asked the referee if he could leave the field of play. Shepherd was allowed to leave and soon after caught his train to Bolton on time. (Arthur Appleton "The Hotbed of Soccer")
He was the first Newcastle player to score more than 30 goals in a season (1909–10, 31 league and cup goals) and repeated the feat the following season (1910–11, 33 league and cup goals). In 1911 Newcastle once again got to the FA Cup final helped by 8 goals in the earlier rounds from Shepherd, however in a home league game against Blackburn Rovers the week before the Final, Shepherd was badly injured in a collision with the Blackburn 'keeper and missed the Final which Newcastle lost in a replay. Shepherd was subsequently out of football for more than a year before playing occasionally for Newcastle in the 1912–13 and 1913–14 seasons. He left Newcastle for Bradford City in July 1914.
He also has a place in FA Cup history as being the first person to score a penalty in an FA Cup Final. At Newcastle he played 123 games, scoring 92 goals, winning a League Championship and an FA Cup final along the way. His other clubs included Bolton Wanderers, Blackburn Rovers and Bradford City.
He was top scorer in the First Division in the 1905–1906 and 1910–1911 seasons.
- England profile
- A Complete Who's Who of Newcastle United, by Paul Joannou.
- Haway The Lads, The Illustrated Story of Newcastle United, by Paul Joannou, Tommy Canning/Patrick Canning.
- The Hotbed of Soccer. Arthur Appleton.