An inside forward, Jack started his senior career with his father's club, Plymouth Argyle, after the war. He played in the Southern League in 1919–20, and was a member of Plymouth's team for their first match in the newly formed Football League Third Division in 1920–21. He scored 15 goals in 48 appearances in all competitions. In late 1920 he returned to the town of his birth, signing for Bolton Wanderers for a world record fee of £3,500 (£ in ). He spent eight seasons with the Trotters, forming a formidable partnership with Joe Smith, and between them they scored more than 300 goals. While with Bolton, he made history by being the first person to score a goal at Wembley Stadium, in the 1923 FA Cup Final; Bolton won 2–0 and Jack earned his first medal.