Jackson began his career as an amateur with
Arsenal before he joined
Leyton Orient at the age of 17. He made 38 appearances in the
Third Division South for
Alec Stock's O's in the
1950–51 season. He impressed in his creative performances at
Brisbane Road, enough so that
Liverpool manager Don Welsh paid £6,500 and part-exchanged
Don Woan to bring the 18-year-old to the club in November 1951. He made his debut on 10 November 1951 at
Anfield in a league match against
Bolton Wanderers; Jackson's first goal for the club in the 61st minute was enough for the "Reds" to get a point from a 1–1 draw. He scored eight goals in 38 games in the
1958–59 season, ad provided many assists as the "Valiants" won the
Fourth Division title. He departed the "Imps" at
Sincil Bank for
Peter Taylor's
Southern League side
Burton Albion. After leaving
Eton Park, he later turned out for
Boston United. ==Style of play==