Jack was Bolton's top scorer in 1896-97 but lost his place in the side and joined Preston North End in 1901. That season he scored 6 goals in 22 games but failed to help his club gain promotion to the First Division of the Football League.
In 1902 Robert Jack joined Glossop. He only played 30 games before joining Plymouth Argyle in the Southern League.
After retiring from playing the game, Robert Jack became manager of Southend United. In 1910 he was appointed to the same position at Plymouth Argyle. He held the post for 28 years. After the First World War he signed his two sons, David Jack and Robert Jack. In 1920 they were both sold to Bolton Wanderers.
Robert Jack died in Southend in 1943.