Jack began his career with Alloa Athletic, making his debut at the age of 15 and turning professional in 1893. He moved to Bolton Wanderers in 1895. He was Bolton's leading scorer in the 1896–97 season with 11 goals. He played a total for 110 league and 15 FA Cup games for the club, scoring 29 goals. He left Bolton in August 1901, following a serious ankle injury. He joined local rivals Preston North End after scoring 29 goals in 110 league games for Bolton. He spent just one season with Preston, scoring 6 goals in 22 league games, before joining Glossop the following summer. After a further 6 goals in 30 appearances he moved to Plymouth Argyle, becoming the club's first professional in 1903. He made his Argyle debut in September 1903 against West Ham United in the Western League. In 1904–05, the club's handbook described him as "our famous flier, probably last season was the best in the player's history".
Managerial career
Following the departure of Frank Brettell, Jack became player-manager of Plymouth Argyle in 1905, 1905–06, and led the club to third in the Western League and fifth in the Southern League. He left the club in the summer to take up the position of player-manager at Southend United. In his first two seasons with Southend they won the Southern League Second Division title, gaining election to the Southern League First Division in 1908. He retired as a player at the end of the 1909–10 season and re-joined Plymouth Argyle as manager, remaining in charge at Home Park until April 1938 when he retired. During his 28 seasons in charge, Jack had guided Argyle to the Southern League title in 1913 and into the Football League in 1920. In their first season in the league they finished 11th in the Third Division, but finished runners-up in all of the next six seasons. They finally clinched the title and promotion in the 1929–30 season. In total, he took charge of 1,093 matches for the "Pilgrims".
Jack lived in Southend during his retirement, occasionally working as a scout for his son David while he was manager at Southend. In addition to David, two of his other sons,, also played professionally for Bolton Wanderers. Despite being Scottish, Jack represented England at bowls for several years, including being Captain. He won the English Bowling Association Singles Championship in 1926. His ashes were scattered over the pitch at Home Park, Plymouth.
