Born in St Helens in 1892, William Caulfield began his career in local football in Ormskirk before joining Southport Central as a Forward for the start of the 1913/14 season. In his first season he scored 13 goals in 35 games. Continuing his second season in the same vein he had noticed 14 in 31 before making a move into the Football League with Blackburn Rovers in Feburary 2015.
Due to the suspension of competitive football following the outbreak of the First World War he failed to make an appearance for Rovers and returned to Central for the start of the 1915/16 season.
He remained with Southport until the summer of 1920 when he joined fellow Central League outfit Crewe Alexandra, initially as an amateur. When Crewe became founding members of Football League Division Three North at the start of the 1921 campaign he signed professional terms. After a successful spell in which he scored just shy of 60 goals, he joined Nelson, newly promoted to the second division, in July 1923.
After an injury hit start to the season which saw him miss the first three months he eventually played 18 times, scoring 5 goals. Despite this he was released by Nelson and made his return to Crewe for a further season before joining Chester in the summer of 1925, where he finished his career.
Billy passed away early in 1972 in Haydock.