He played in 30 League matches over two seasons at Rangers, before signing for another First Division club, Port Glasgow Athletic, at the start of the 1908–09 season. 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. He joined Hamilton Academical for what remained of the season.