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Jackson was appointed first team coach at St Mirren in June 2018, but left in September following the departure of manager Alan Stubbs.

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 and former Celtic teammate McNamara – recently appointed as manager of Dundee United – as a coach. While at the club, United lost the 2014 Scottish Cup and 2015 Scottish League Cup Finals. Jackson left Dundee United in September 2015, following McNamara's departure. Three months later he was declared bankrupt. He then served as assistant manager to Gary Locke at Raith Rovers, until both were sacked by the club in February 2017.

In January, Jackson joined Livingston on a month's loan, subsequently extending it until the end of the season. During this time, Hearts released him from his contract. After winning the First Division title with Livi, scoring one goal in the process against Falkirk, Jackson was not offered a permanent contract. He returned to the Premier League with St Johnstone on a one-year deal. Jackson made nine league appearances for Saints, scoring once against Dundee, before being allowed to join Clydebank on loan in January 2002, where scored a début goal in a 1–0 win.

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, he 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.

He was 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.

He moved to Celtic in 1997 as Wim Jansen's first signing, but soon had to be 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 fell out of favour and had a spell on loan with Coventry City. He scored Celtic's first official goal in the revamped UEFA Champions League competition in 1998.

Jackson won 28 caps for Scotland, scoring four goals. Making his début in March 1995, Jackson was also in the starting line-up for a fixture against Estonia in Tallinn in October 1996, but a scheduling dispute meant the home team did not adhere to a quickly-rearranged afternoon kick-off time, and the match was abandoned at kick-off with no caps awarded to the Scotland players; the fixture was re-arranged for the following February, but Jackson was not selected.

Jackson joined Hibernian in 1992. During his five years at Easter Road, he was a runner-up again, this time in the 1993–94 Scottish League Cup.

He returned to Scotland in late 1988 with Dundee United. After being ruled out for six months of his first campaign with a broken ankle which initially went undetected, Jackson spent four years at Tannadice, picking up a 1990–91 Scottish Cup runners-up medal and finishing that season as the club's top scorer with 18 goals.

Jackson began his career in 1985 with Meadowbank Thistle in Edinburgh, while he worked in a part-time job as a printer. Twenty-two league goals won him a move south. After 9 games at the outset of Meadowbank's 1986–87 league campaign he joined Newcastle United in October 1986. Jackson made his Newcastle debut as a substitute for Ian Stewart in a 2–1 defeat at home to Arsenal on Saturday 18 October 1986, in which he won a penalty for his side. In two years with the Magpies, Jackson scored seven goals.

Darren Jackson (born 25 July 1966) is a Scottish former professional footballer, who played predominantly as a forward. Jackson played for several clubs in Scotland and England, including Newcastle United, Dundee United, Hibernian, Celtic and Heart of Midlothian. Jackson played 28 times for Scotland and was selected in their 1998 FIFA World Cup squad.