Preston, Lancashire born inside right Jack Holland began his senior career with hometown First Division club Preston North End joining them in 1919 and turning professional in July 1920, and made his Football League debut against Derby County in January 1921, making 6 appearances in his debut season but only 2 more thereafter. He joined Swansea Town in June 1923 where he scored 3 times in 24 appearances of which only 5 were in their Third Division (South) Championship winning season of 1924-25.
In May 1925 he joined Wrexham but after 2 goals in 9 games Holland was soon on the move again, to Crewe Alexandra the same December. He scored 3 goals in 23 appearances for The Alex but moved to Newport County in June 1926, where he scored twice in 10 appearances over the following season. In October 1927 he joined Second Division Clapton Orient scoring 4 goals in 19 appearances, but after they were relegated in 1929 he was released and joined Carlisle that July. At Brunton Park he enjoyed the most productive spell of his career, scoring 13 goals in 35 appearances, but he moved on again joining Barrow in July 1930, playing 7 times later the same year before finishing his football career with non league Darvel who he joined in May 1932.