Bedminster, Bristol born centre forward Jack Milsom began his football career with Hopewell Hill Mission in 1925 and after a trial with Exeter City, joined Bristol Rovers in August 1926, spending 1926-27 on their books without making a first team appearance. In 1927 he joined Kettering Town before being signed by Rochdale in July 1928, making his Football League debut at Barrow the next month, scoring in a 3-3 draw. Milsom was Rochdale’s leading goalscorer with 26 goals in his debut season, and his goalscoring feats brought him to the attention of First Division Bolton Wanderers, who bought him for £1,750 in December 1929 after 40 goals in 56 appearances.
He initially struggled to get into The Trotters’ first team, making only 10 appearances in his first 18 months at the club, but became a regular in the first team from December 1931, after which the goals flowed with regularity. That season he notched hat-tricks against Sheffield United, Blackpool, and scored 4 times against Liverpool. He was the club’s top scorer with 19 goals, repeating the feat with 27 goals the next season, despite which Bolton were relegated. Indeed he was the club’s top scorer for the next four straight seasons, making 6 straight in total, including scoring 35 times as Bolton won promotion back to the First Division in 1934-35 as Second Division runners up.
In February 1938, after an incredible 153 goals in 255 appearances for The Trotters, he was signed for £4,000 by a struggling Manchester City side trying to avoid relegation the season after having won the League Championship. He could not prevent it. He continued to play for Manchester City until the outbreak of the Second World War, scoring 24 goals in 35 appearances for the Maine Road club. His most notable feat was scoring 7 goals in successive days against Tranmere Rovers in December 1938, 4 in a record 9-3 away win on Boxing Day, and a hat trick in a 5-2 home victory 24 hours later. During the Second World War he continued to play wartime football for City, and guested for Bristol City and Fulham before retiring in May 1943.