He has also worked as an agent and a coach.
Jackson began his career in 1985 with Meadowbank Thistle, while he worked in a part-time job as a printer. Twenty-two league goals won him a move south.
He joined Newcastle United for a £40,000 fee. Jackson made his Newcastle debut as a substitute for Ian Stewart in a 2–1 defeat at home to Arsenal. In two years with the Magpies, Jackson scored seven goals and returned to Scotland in 1988 with Dundee United.
Jackson spent four years at Tannadice, picking up a 1990-91 Scottish Cup runners-up medal.
Jackson joined Hibernian in 1992. During his five years at Easter Road, Jackson was a runner-up again, this time in the League Cup.
He moved to Celtic in 1997, but Jackson was treated for hydrocephalus that required surgery in September 1997. He was playing again within three months as Celtic went on to win both the League and League Cup. The following season, Jackson had a spell on loan with Coventry City.
He next joined his boyhood heroes Hearts.
In July 2000, Jackson revealed he intended to move into management once his playing career finished. In October, Jackson was barred from playing for Hearts due to the impending trigger of a clause enforcing a one-year extension to his contract, seeing him discuss a possible return to former club Dundee United. After United signed Charlie Miller instead, Jackson negotiated a deal to return to first-team action at Hearts, only to find himself surplus to requirements when Craig Levein was appointed three weeks later.
In January, Jackson joined Livingston on a month's loan, subsequently extending it until the end of the season. During this time, Hearts released Jackson from his contract. After winning the First Division title with Livi, Jackson was not offered a permanent contract.
He returned to the Premier League with St Johnstone on a one-year contract. Jackson made nine league appearances for the Saints before being allowed to join Clydebank on loan in January 2002, where scored a début goal in a 1–0 win.
Jackson won 28 caps for Scotland, scoring four goals. Making his début in March 1995, Jackson was also part of the Scotland squads for UEFA Euro 96 and the 1998 FIFA World Cup, playing in two of the World Cup matches. Jackson played two further games after the tournament, appearing in the UEFA Euro 2000 qualifying matches against Lithuania and Estonia.
Despite Jackson's earlier vow to move into management, he became an SFA agent representing players including fellow Scots Jackie McNamara, Mark Wilson and Steven Thompson. In February 2013, Jackson relinquished his agent status to join client Jackie McNamara – recently appointed as manager of Dundee United – as a coach. Jackson left Dundee United in September 2015, following McNamara's departure. He then assisted to Gary Locke at Raith Rovers, until both were sacked by the club in February 2017.
Scores and results list Scotland's goal tally first.Dundee United
Scottish Cup Runner-up: 1
Scottish League Cup Runner-up: 1
Scottish Premier Division: 1
Scottish League Cup: 1
Scottish First Division (second tier): 1