Jackson was born in Cambuslang, Lanarkshire, Scotland, but his family emigrated to Australia when he was two. The young Jackson grew up in New South Wales and played football as a youth. He is believed to be the youngest player to have appeared in senior football in that country, having played for Hamilton Athletic in 1889 at the age of 13 years 7 months. He remained with Hamilton for the 1890 season, then in 1891 he moved on to Adamstown Rosebud.