Jack began his career with Alloa Athletic, making his debut at the age of 15 and turning professional in 1893.

He played a total for 110 league and 15 FA Cup games for the club, scoring 29 goals.

[2] 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 returning home for a short spell with Alloa at the start of 1902/03, then joining Glossop in late September.

[2] He made his Argyle debut in September 1903 against West Ham United in the Western League.

In addition to David, two of his other sons, (Rollo and Donald), also played professionally for Bolton Wanderers.