St Helens, Lancashire born inside right Billy Caulfield began his football career with Ormskirk in 1912, from where he joined Southport Central in 1913. After two seasons at Haig Avenue he was signed by Blackburn Rovers in February 1915, but didn’t play for them before the First World War forced the abandonment of peacetime football at the end of the season.
In 1919, Caulfield returned to Southport (the club had by now dropped “Central” from its name), who by then were playing in the Central League. After one further season at Haig Avenue he moved to fellow Central League outfit Crewe Alexandra in the summer of 1920, initially as an amateur player. Crewe were founding members of the Football League Third Division (North) at the start of the 1921-22 campaign, and Caulfield signed a professional contract with the club in the summer of 1921. He made his Football League debut in The Railwaymen’s inaugural League fixture at Tranmere Rovers in August 1921, scoring their first League goal albeit in a 4-1 defeat. He was Crewe’s leading goalscorer in 1921-22 with 21 goals during the campaign, including 4 goals in a 5-1 victory over Stalybridge Celtic in January 1922. Over two seasons at Gresty Road, he made 64 appearances for Crewe, scoring 25 goals.
In July 1923 Caulfield joined Nelson, who had just been promoted to the Second Division for the first time in their history. During pre-season training he suffered a groin injury that forced him to miss the first three months of the campaign. When Caulfield eventually made his debut for Nelson on 3td November 1923, he scored two goals in a 3-0 win over Coventry City at Seedhill. During the remainder of the 1923-24 season, he played 18 further matches and scored a total of five goals. In September 1924, Caulfield was released by Nelson and returned to Crewe Alexandra. In a solitary season with the side, he made 31 appearances mainly as a right winger without scoring. In the summer of 1925, Caulfield joined Cheshire County League club Chester, his final club before his eventual retirement.