He ended his career with spells at four more Scottish League clubs: Port Glasgow Athletic, Hamilton Academical, Morton and Abercorn.

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.

[11][12] He made his debut against Leicester Fosse on 2 September 1899, and for the next six seasons he was a regular at the club, playing either at left back or wing half.

[12][13] He came closest to international recognition while with Arsenal, playing in the March 1905 edition of the Home Scots v Anglo-Scots annual trial match.

[20] In January 1910, Jackson refused to play in a Scottish Cup tie because he was claimed he was owed considerable arrears of wages, of some £21; the club duly fined him £20 and suspended him to the end of the season.

The Scottish Football Association ruled in Jackson's favour as to wages due up until his refusal to play, but confirmed the club fine.